Looking for some of the best opening lines for online dating sites and apps?

The online dating world is competitive, especially for men. That’s why it’s important that you grab a girl’s attention fast. Besides setting up a killer profile, you need to have some great online dating openers ready to intrigue her. 

During my 100-date experiment, I analyzed thousands of dating profiles. When you deliver awesome opening lines for online dating sites and apps, your chances of connecting with quality women increase greatly.

On the other hand, when your online dating openers fall flat, you’re basically guaranteed a hard left swipe.

But don’t worry. I’m here to help. Below, I have listed 31 of the top opening lines for online dating sites and apps. I’ve used my expertise to create these lines so that you don’t have to stress about it. And to keep you on track, I am also including an explanation on why certain lines work.

However, before we get into that, I’d be remiss if I didn’t offer some examples of what I consider the worst online dating openers. Avoid using these types of lines at all costs:

• Anything explicitly sexual

• “DTF?” NO!

• Snarky comments

• Negative openers. Women want positivity, so exude that in your messages

• TMI. No one needs to hear about how crazy your ex-girlfriend is or how alimony has been a real b**ch since your divorce. Save super personal stuff for if you get to a third date.

• “Hey,” “Hello,” or “How are you?” While these are certainly benign, playing it safe doesn’t mean you’re being strategic. Don’t open with something generic or boring.

Now that we’ve gotten that out of the way, onto the…..

30 Best Opening Lines for Online Dating and Dating Apps

#1: Ask her a question about a passion of hers….

Take a good look at the question my test user sent to a Facebook Dating user in the above screenshot. It reads: “how would you end homelessness?”

Then see this woman’s 15 line response!!

Boom, a huge success. Here’s some reasons why my test user’s opening line is so powerful: 

• He asked a question and ended with a ?.

• The question is about something the female user is passionate about. 

• The female user realized my test user took time to read her bio. 

Guys, the clients of mine who have the most success always take the time to at least scan dating profiles of women who they’re interested in. They look for commonalities to try and create an emotional response. That’s the goal.

Now scroll through the below questions. Don’t just pick out a question and send at random.

If you see that a woman is super active, then send her question #3. If you see that she loves dogs, send her question #6. You’re always welcome to customize the below lines. 

#2: “Serious question for you. Best discovery — avocados or Amazon?”

This line is an example of either/or questions. I love using these types of openers because it’s fun and prompts an interesting conversation. Also, this example offers a dash of humor. Whenever you can insert something witty, do so.

Line #3: “Which do you like better, hiking or biking?”

This is another example of an either/or question. However, the strategy here isn’t to break the ice by making her laugh. If she lists that she likes being active (hence the hiking or biking question), ask her what activity she likes best.

When you find out, you can craft a compelling date idea based on her answer.

Line #4: “If you were a fruit, you would be a fine-apple. Correction: An organic fine-apple.”

Now, you really need to gauge a woman’s sense of humor before going the cheesy pickup line route. This is one of the many reasons I encourage guys to read a woman’s complete profile before messaging her. Her profile is basically a guidebook on what types of things would be good to mention in an opening line and continued messages. Moreover, her listed interests are what you should use to plan the first date with her.

If she comes off as quirky and seems like the type that would chuckle over this type of line go for it. This type of opening line would work especially well if you meet her on Green Singles or if her profile indicates that she is very health-conscious.

Line #5: “Do you read Dr. Seuss? Because Green Eggs and DAMMMNNN!”

Like the third line, this is one that can be successful if she seems like someone who would enjoy this type of humor.

Line#6: “Question: Big dogs, little dogs, or this dog?”

In this opening line example, you would then post a picture of your adorable dog (or a friend’s) to compel her to respond. Cute animals are always a win.

Line #7: “Capo’s is where it’s at. Have you ever been to Grinders?”

If you live in San Francisco, you may be familiar with Capo’s. It’s an awesome place that serves Chicago-style pizza. Grinders is another place that serves deep dish pizza.

This example is drawing from something a woman listed as an interest in her profile and asking an open-ended question. You don’t have to use Capo’s, obviously, when you message a girl. But everyone loves to eat, so if she has a food-based interest in her profile, run with it.

Line #8: “Before we get to know each other, I just need to put it out there that I will kill all the spiders for you.”

No one wants to be caught alone in a room with a spider. Knowing you would be her knight in shining armor is a great and playful way to open*.

*Note: Don’t use this line if she has a pet tarantula.

Line #9: Don’t Use a Line, Just This Gif

When in doubt, gifs can make great opening lines on dating sites and apps.

Line #10: “So I guess this means we’re exclusive now, right? ;)”

This is a great way to flirt and be playful in your opener.

Line #11: “Anchorman was a great one — a classic, really. So what do we think about the sequel? Yay or nay?”

You don’t have to mention Anchorman, but any comment you can make regarding a movie or TV show she likes is a good icebreaker.

Line #12: “I love [insert comedian she likes here]! Have you seen [insert similar comedian here] do standup? He’s pretty rad as well.

Line #13: “You look like you could make any outfit work, but that cold shoulder just doesn’t suit you.”

This isn’t so much an opening line as it is a good response if you get radio silence back. I suggest always trying to overcome an objection a couple times before moving on.

Line #14: “Favorite comedian, actor, and singer? Go!”

This is another way to build rapport by finding shared interests.

Line #15: “I just want to let you know straight away that I don’t send unsolicited dick picks. I do send unsolicited duck pics.”

Line #16: “I don’t mean to brag but I happen to be very good at opening jars.”

Like killing spiders, this is something that will never go unappreciated.

Opening Line #17: “I hear you like bad boys. I’m bad at everything.”

Line #18: “That’s awesome that you’re into [insert famous artist here]. There’s actually an exhibit on him this Saturday if you’re interested.”

Once again, I’m throwing in an “art” thing for the sake of an example. But you can use anything as long as it’s based on an interest listed in her profile.

When you hone in on an interest, use this to move toward a TDL. A TDL is what we here at EmLovz refer to as a date’s call-to-action. It stands for Time, Date, and Location.

Don’t wait too long during an online dating conversation to ask a woamn on a date that is based on her interests and offers a specific TDL. Doing this will make it way more likely for her to agree. Women, in general, like it when a man initiates things as far as a first date goes. If you cut to the chase and have a cool date idea ready, she will probably find it very refreshing and be more compelled to meet you.

Line #19: “You had me at cold cuts.”

This is assuming a girl said she loved cold cuts. But really you can use the “You had me at…” for anything and just insert an interest.

Line #20: “I’ll binge watch [insert show she loves here] with you anytime.”

Line #21: “Has anyone ever told you that you look like [insert actress/famous person she resembles here]? Only that you’re a lot better looking?”

Line #22: “I will brunch so hard with you if you let me.”

Women. Love. Brunch.

Line #23: “Do you think it’s strange when men say they’re fans of The Bachelor? And can you tell that this is my way of telling you I’m a fan of The Bachelor?

Don’t be shy about your love of #BachelorNation. We’re always looking for someone new to join the viewing party.

Line #24: “If you were stranded on a desert island, what is the one thing you would have to have with you?”

Line #25: “Typical us, right? Me writing you messages and you not responding?”

This is a cheeky way to message her if she’s gone radio silent on you. Remember, you need to try to overcome her objection two times before moving on. So if she doesn’t respond to this line, follow up with…

Line #26: “I’m at [insert number here]. Give me a call if you want me to take you to get the best deep dish pizza you’ve ever had ;)”

Line #25: “When is the last time you sang to yourself or to someone else?”

Line #27: “You’re cute, but are you friendly?”

This is another playful line that can lead to some fun, flirty banter.

Line #28: “What are you most proud of in life, but never have a chance to share with other people?”

Don’t be afraid to dive a little deep. You don’t want to get overly personal, but a question like this can be a great way to allow you both to open up. Before things go too far, find a good point to ask a date using a TDL and you can continue these types of conversations face-to-face.

Line #29: “Are you a morning person or a night owl?”

Hey man, commonalities matter. What if you move in to a small 1 bedroom apartment with said girl and she’s up until 3 am while you gotta get up at 6am for work? 

Line #30: “Let’s just skip to the important stuff. Britney Spears or Christina Aguilera?”

If her dating profile has concert pics this may be a good line to get a laugh out of her. 

Line #31: “Should we talk for a while or do you want to just cut to the part where I take you out on the best date you’ve ever had?”

This may be a great line for my east coasters out there. 

Line #32: “Molly, will you accept this rose? 

What woman doesn’t love The Bachelor and want to be swooped up by Prince Charming? 

Want More Opening Lines for Online Dating Sites and Apps?

If this list wasn’t enough for you, make sure to checkout a couple other articles of mine that are similar….

I also provide personalized coaching services via Skype. If this is more your style, then head over to my calendar and book a 1-on-1 session with me today. 

During our introductory session, we will come up with a dating action plan that is tailored to your personality, concerns, and needs. We’ll also discuss my 3 month coaching program to see if it’s a fit for you.

In a space already oversaturated with "heys" and low-stakes "lol sup" messages, coming up with the right thing to say on dating apps can be hard. How do you start a chill conversation without overthinking things?

Thanks to a general rut with *looks at hand* "casual dating," I decided to let Carrie Bradshaw run my dating life for a day. The rules were simple: I'd only talk to guys using the OG HBO queen's most iconic (or cringeworthy) lines. The results? Much like the show's breaking of the fourth wall, there were inconsistencies.

1. The Martini Man

A very fair answer to an iconic line, TBH.

2. This guy who man-splained monogamy.

If a tree falls in a wood and no guys are there to unpack monogamy as a concept, did it really happen?

3. This people-pleaser.

Thank you, I know it's asking a lot.

4. The guy who witnessed the most embarrassing autocorrect typo of all time.

You and me both, buddy.

5. This guy who was quick to call me TF out! Damn!

I respected him for calling me out until he circled back 21 hours later with that last bit.

6. Mr. Fifty Shades of Silver

Honestly, my own fault for expecting anything less from a dude who used ";)" and "Lol" (with a capital L — everyone knows "lol" lowercase is ironic and Cool)

7. The guy with the panda suit.

Is the panda thing a race thing or what's up with that?

8. The (only) guy who figured it out

He negged me by calling me a Miranda and honestly, it worked. I gave him my number, and he ended up FaceTiming me immediately, so love is truly dead.

9. The Shakespeare enthusiast

Cool ... I too had to read Hamlet in the 10th grade.

10. The man who was ... intrigued

I love when guys say fancy shit like "intrigued" online because you know IRL he doesn't even say anything when he flips you over halfway during sex. But yeah, tell me how intrigued you are, old sport.

11. This ... guy

A good ... sport.

12. This realist

I mean, it's kinda true.

13. The "pro-dildo" guy

Bummer that I was in such a rush to whip out one of Samantha infamous sex lines that I didn't even read what he had said correctly. But good to know that this guy is proudly "pro-dildo." I don't know any women who are "anti-masturbation" for men but I do plenty of guys who think they're special snowflakes for acknowledging that women masturbate.

14. The man who thought I was fake.

No, sparkle-emoji-user, I am very real!

15. This defeatist.

Sigh.

In the end, I was thankful for Carrie's lines. Having a script erased a lot of the pressure I feel when trying to drum up conversation with a stranger. The experiment underlined the fact that most guys are at least willing to try with conversation — even if they're just doing their best to respond to weird, cryptic monologues. If so many people will vibe with Carrie's corny ass, it's not like I'm going to be hella judged if my opening joke doesn't land.

The emotional one-liners were also really fun, because who among us isn't looking for a soul mate? Women especially spend a lot of effort trying to look chill and casual ("Hahaha, I also am dating, like, six other people right now, lol, it's cool! Don't worry, I definitely did not talk about you like you were my boyfriend to my family or anything!"). Using Carrie's quotes was a fun way to vicariously live out any and all no-chill fantasies I had about leading with my true monogamous freak flag.

I will admit that I felt a little guilty about the experiment at first. I'm someone who is baseline always a little scared that guys are trolling me (Is every hot guy who's ever hooked up with me just doing so for some sick She's All That-like bet?). But then I remembered the guy who took Carrie's infamous "some women aren't meant to be tamed," line as an OK to segue into talking about handcuffs, and then I don't feel that bad.

Update: Yes, I know, I know, the blow job quote is from Samantha Jones and not Carrie herself, it has been corrected. It was just too iconic not to try.

Follow Carina on Twitter and Instagram.

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Downloading a dating app is the easy part. What’s not easy is sweating over the pictures that best represent you (or the ones you want to present to hundreds of single women). It’s also not easy to painstakingly craft a bio that’s equal parts informative and humorous.

But toughest of all? Coming up with that first perfectly witty message the minute you match with someone decent. These days, now that women have seen and heard it all on dating apps, making a lasting first impression seems freaking impossible.

So we asked 20 real women to divulge the perfect one-liners, questions, and messages they wish men would send on mobile apps or dating sites. Oh, and by the way: ‘Hey, what’s up?’ isn’t cutting it. But cheese references might. (No, we don’t get it either.)

Here’s what they said:

“I like when a guy tries to get off the app immediately and says something like, ‘Hey, I’m interested in getting to know you. If you’re down, shoot me a text (insert #).’” – Cara J.  

“Run with something I have on my profile. Personally, I’m obsessed with cheese. The perfect first message would be something like ‘Saw you’re a cheesehead. I’ve been dying to go to this Italian place that serves four-cheese gnocchi—or pairs wine with half a dozen local cheeses. Interested?’ Um, yes, yes I am. Because A) who wouldn’t be into that? And B) you took the time to be unique. Even if we start messaging and I come to find you’re a wackjob and cancel the date, you still astronomically upped your chances than the guy who sent ‘Hey.'” – Victoria G. 

“Something related to my profile or picture that’s relatable. I’ve had a guy say: ‘I’ve been skydiving before, but how incredible was jumping in New Zealand?’ because of a photo I had. I feel like that’s the easiest way to connect with someone—through shared interests.” – Rae P. 

“‘Top 3 things you can’t live without—ready, set, go.’ Disarm me, throw me off (without being creepy), and be original. I’ll be way more inclined to play along. And this shows you actually have a personality…or at least a semblance of one.” – Anne S. 

“I’m actually totally cool with ‘Hey! How’s it going?’ It’s more grown-up and confident than ‘What’s up?’” – Sasha B. 

“Bring up something that’s in my bio or one of my pictures you relate to. Perfect example: ’Hey, What kind of race were you doing? I’m big into fitness, too.’ It shows you’re interested in learning about me (rare among dudes). Remember, the conversation shouldn’t be one-way. And we get to skip the small talk and get right into the conversation.” – Marie L. 

“I’ve actually gotten funny memes as a first message. The one that made me die laughing was a cartoon with pounding heart eyes—basically saying he thought I was attractive but not in a completely weird way. It’s just a better icebreaker than ‘Hey.’” – Samantha M. 

“Start with something like: ‘Totally into your profile and interests. Where were you traveling to?’… or, ‘How long did you live in San Francisco for?’ Target bits and pieces of my profile. I chose to highlight them for a reason!” – Caitlin D. 

“I honestly like a simple ‘Hey, how’s your day going?’ Ultimatums like, ‘Coffee or sleep?’ or ‘You’re gorgeous.’ annoy and freak me out.’” – Amy S. 

“Send a question that relates to something from my profile. It shows you actually took the time to craft a response and didn’t just send a generic ‘Hey, what’s up?’ to every girl on the app. For example, if one of my photos was of me at a concert, make a connection to a concert you recently went to.” – Caroline T. 

“I think the perfect first message is direct. ‘Hey, you seem really interesting. Would love to go out sometime.’ Stay away from stupid pickup lines.” – Rachel D. 

“Point out how awkward dating apps are and poke fun at yourself without being too self-deprecating and blindingly insecure. Say something like, ‘Trying to come up with a clever one-liner to hit you with gave me more anxiety than the SATs. So I’m just gonna go out on a limb here and say I would love to get to know you outside the confines of this app.’ You seem sincere and I’m WAY more likely to want to get to know you, too.” – Brielle A.

“Always something witty or about food. Or, start with a question about my pictures or bio. I have a lot with my nephew because he’s important to me.” – Laura W. 

“Something that makes fun of the app and the situation. Like, pretend to be a character from It’s Always Sunny in Philadelphia and say, ‘Hey, I’m Charlie. I like cheese and live with a guy named Frank.’ I would respect that. Though if I didn’t get the reference, then this would just flop.” – Amanda H.

“I like when a guy is engaging. It might be a little overdone, but asking for two truths and a lie is still, to me, a great conversation starter.” – Laura Q.

“Something unique and also relevant to my life via my profile. Ask, ‘Hey, what kind of nurse are you?’ It shows you’re generally interested in getting to know me as a person—not just what I look like. Anything beats ‘Hey, good lookin’.’” – Vanessa P. 

“‘Your perfect Sunday morning: workout, movie, or brunch?’ Depending on my answer, ask: ‘If I play my cards right, would you like to join me for X, Y, or Z sometime?’ This is PERFECT. It’s clever and not too demanding or creepy, because it’s on me to decide when or if it actually happens. If our conversation goes well and I’m feeling you, then I can initiate picking a date.” – Candice H. 

“I like for a guy to show his personality and humor. My now-boyfriend initiated a conversation with: ‘I don’t break apart Kit Kat bars. I eat them whole. Is that a deal breaker?’ I thought this was so weird and funny, I responded immediately.” – Marissa D. 

“Anything that makes you seem not like a complete stranger. Make a connection. I’m a law student, so if a guy draws a connection to the fact he’s in grad school or asks about it, it creates instant dialogue.” – Marianna B. 

“Compliment me on anything but my appearance. Say I fascinate you or you love that I’m really outdoorsy. Guys need to stop defaulting to cheap wins. We see past that—especially if we’re on here to find an actual relationship.” – Rose T.

You probably already know Tinder messages like this just aren’t cutting it:

For most guys, the biggest challenge on Tinder isn’t getting matches – it’s getting the most attractive women to respond to your icebreaker.

Steal our top-performing Tinder openers and immediately boost your response rate by 413%! [Download Free Playbook]

Being funny can give you an edge because women are genetically programmed to find a sense of humor irresistible in a man.

Of course, for that particular science nugget to work, you have to actually be funny.

Tinder Message #1:

The hotter she is, the more choosy she can be when it comes to responding to Tinder messages.

Tinder Message #2:

Surveys have shown that for the majority of women, a sense of humor is the #1 desired trait in a man. This is why funny always trumps boring in a Tinder conversation.

But humor can be tough to pull off because it’s so subjective.

What one woman thinks is hilarious might fall flat with the next. If you aim for laughs but land in eye-roll territory, don’t hold your breath waiting for a response.

Don’t worry – today you’re going to discover 9 funny tinder messages that work extremely well, like the two featured above.

And as an added bonus for reading to the end, you'll even get 3 tips that will get you 3x more Tinder responses!

Watch Your Response Rate Soar With Funny GIFs

Some things are inherently funny and difficult to resist, like fluffy puppies and other animals doing silly things.

Plus, a bear waving hello works no matter what a person's profile says, so you can use it repeatedly.

According to Tinder, not only does including a GIF in your message boost your response rate by 30%, the resulting message exchange is likely to last twice as long.

Tinder Message #3:

But on dating apps, simply sending a GIF for your first message isn't enough.

Don't put the burden on your Tinder match to actually start the conversation, because that’s work.

Instead, make it as easy as possible to respond by asking her an interesting question in a humorous way.

Taking control of the conversation is a confident, sexy move she’ll appreciate.

Tinder Message #4:

Tinder Messages That Unleash Your Creative Side

You don’t have to rely on GIFs to create funny opening lines for Tinder.

Tinder Message #5:

You can be funny with just words too.

Tinder Message #6:

Just make sure to follow these three rules for sending Tinder messages:

1. Keep it PG-13, even on Tinder. Vulgarity from a total stranger is an instant turnoff.
2. Ask her a question. The more effort it takes a woman to reply, the more interested she needs to be to actually do it. If you want to maximize your response rate, make responding to your conversation starters effortless. And if responding is entertaining, even better…
3. Make her feel something. Amused, entertained, intrigued – when your opening message evokes an emotional reaction, chances are she’ll be way more likely to respond.

When writing back to that charming guy with a good sense of humor seems effortless and enjoyable, a response is practically guaranteed.

Tinder Message #7:

Go With What Works

When you find funny Tinder messages that work for you, be green and recycle them.

Tinder Message #8:

There's no need to reinvent the wheel each time you have an attractive match and want to start a conversation.

You can even send seemingly custom messages to women who reference certain topics like having a dog in their bio or photos.

Tinder Message #9:

The average guy is already spending 1½ hours a day on Tinder, so why spend even more time coming up with new material?

To truly be efficient with your online dating time, it’s important to figure out which messages work best for you.

That means you need to track each time you send a specific icebreaker message, and each time it gets a response.

Sound like a pain in the butt? Kinda, but the results are well worth it.

And our response rate calculator makes it pretty easy to do. With enough data, you’ll definitively know which Tinder openers you should send to more women.

With Messaging, Timing Is Everything

There’s another easy way to optimize your results on Tinder.

Send her the message during the times she’s most likely to respond. Here at VIDA, we’ve found early evening works best, just as she’s getting home from work.

The data crunchers over at Nielson agree – their data shows Tinder’s peak activity is in the evening, between 5pm and midnight:

Good timing is more than just what hour of the day you send your icebreaker. You also need to nail the timing when it comes to her response.

If you pounce on her message and reply within mere seconds of getting it, that looks desperate.

Like you’re literally staring at the Tinder app, waiting for the messages to roll in.

But you’re a busy guy with an active social life (or at least you want her to think you are), so respond like one.

That being said, you also want to look like a guy who’s actively engaged with the app and making himself available for matches he’s interested in.

So while waiting an hour or two is often a good idea, taking more than 24 hours can be suicidal.

Tinder conversations tend to have a short shelf life. It’s on you to keep the momentum going and steer the conversation towards getting her phone number or arranging to meet her in person.

What To Do If She Doesn’t Respond

Rule #1, don’t take it personally. There’s a lot of factors at play here, and not all of them have to do with you.

But if you’re using these examples and not getting a response at least 80% of the time, then you need to take a hard look at your overall Tinder profile, specifically your photos and your bio.

Anytime a girl doesn’t respond to your first message, write her again.

You can send her a light-hearted, funny follow up message like this a day or so later:

If it’s still crickets after the second message, let it go.

While sending a third message will get you some responses here and there, the line between being persistent and being a stalker is very fine.

You probably don’t want to come off looking like this guy, right?

The Easiest Way To Meet Women On Tinder

There’s no denying that being funny gets you noticed, whether it’s sending a humorous message or catching her eye with a witty profile.

But for most Tinder users, adding that extra pop of humor = a lot more work.

And if you’re like the average guy, you’re already spending way too much time on Tinder and wondering when all that swiping is going to turn into some actual dating.

Why struggle when VIDA’s professional writers already have a stockpile of comedic gold?

Even better – we can write a funny bio that’s 100% you, send out our top performing icebreakers, and keep the humor going in the back and forth message exchanges.

And it doesn't stop with Tinder – VIDA can help manage any dating sites and apps you want to use!

The most attractive local women will be excited to meet you – and all you have to do is show up for the dates.

Click here to get started!

Every morning I wake up to the same routine. I log into the Tinder account of a 45-year-old man from Texas—a client. I flirt with every woman in his queue for 10 minutes, sending their photos and locations to a central database of potential “Opportunities.” For every phone number I get, I make $1.75.

I’m what’s called a “Closer” for the online-dating service ViDA (Virtual Dating Assistants). Men and women (though mostly men) from all over the world pay this company to outsource the labor and tedium of online dating. The matches I speak to on behalf of the Texan man and other clients have no idea they’re chatting with a professional.

It shouldn’t come as a surprise that these ghostwriting services exist. Tinder alone produces more than 12 million matches a day, and if you’re a heterosexual American, you now have a one in three chance of meeting your future husband or wife online. But as e-romance hits an all-time high, our daily dose of rejection, harassment, and heartbreak creeps upward, too. Once you mix in the vague rules of netiquette and a healthy fear of catfishing scams, it’s easy to see why someone might want to outsource their online-dating profile to a pro, if only to keep themselves sane.

But where does the digital social assistant end and the con artist begin?

The online seduction manual 

When I tell people that I work as an online-dating assistant, their initial reaction is of morbid curiosity. “How did you even find out about that?” they ask, voices lowering, leaning in.

In November 2017, I ran across an ad seeking “people with good Tinder skills” for a job as a “Virtual Dating Assistant.” At first I thought it was a joke, but I completed their online form out of pure fascination. I received a callback three days later.

Could I work in an “moral gray area?” Would I be comfortable ranking clients’ photographs? Was I dating anyone currently?

Apparently, professional writers make for good online-dating assistants; knowing how to seduce strangers with the written word is the company’s mandate, after all. But the intake interviewer seemed just as interested in my ethical flexibility as he was in the journalistic details of my résumé. Could I work in an “moral gray area?” Would I be comfortable ranking clients’ photographs? Was I dating anyone currently?

I learned that there are two main types of writers at the company: “Profile Writers,” who create seductive and click-worthy profiles based on facts our clients have supplied about themselves, and “Closers,” who log in to clients’ dating accounts at least twice a day to respond to messages from matches.

Despite hiring writers to do this work, virtually none of what the company does requires creativity of any kind. Profile Writers follow strict guidelines, often recycling the same half-dozen clichés over and over again. If a client has a dog (jackpot!), all the Profile Writer needs to do is search for the word “dog” in their manual and choose from a list of dog-related one-liners, like this one:

“Hey. As an animal lover, I want to find out your opinion… dressing up your dog: yes or no?”

The process for Closers is a bit more complicated. The initial training period lasts several weeks before we’re given access to clients’ accounts, during which we must read several training manuals and submit draft responses to fake matches. At first, my trainer encouraged me to get creative with my replies, but by the third week, I was still getting back extensive rewrites. My most frequent mistake was asking career-oriented questions, which were deemed too difficult for some women to answer. “She seems more simple,” my trainer would write in response. “Let’s try a different approach.” My meaningful questions would disappear from our shared GoogleDoc, replaced by simpler, condescending small talk.

My Closer manuals were written by the company’s founder, Scott Valdez, a self-taught dating expert with a background in sales. The manuals have titles like Women On Demand and The Automatic Date Transition, and are loaded with his personal insights into the primal female brain. We are to treat them as dating-assistant gospel.

“There’s no question about it,” reads one chapter, “women want to date the alpha male. They are naturally drawn to the ‘leader of the pack.’” Valdez elaborates later in the manual: “The alpha male is the selector, he chooses… he is not chosen.” But how do you present yourself as an Alpha? “Never compliment her without a qualification,” he writes. “Let her know what you want in a woman and make her explain why she fits those criteria.”

“I’m not a psychologist or self-proclaimed expert in the multiple facets of human psychology,” Valdez told Quartz in a phone call. “I consider myself to be a marketer, a matchmaker, and a dating expert.” He lists the books he’s read that inform his methods: Malcolm Gladwell’s Blink, Dan Ariely’s Predictably Irrational, David J. Lieberman’s Get Anyone To Do Anything, (“which kind of scared my mom”), and the classic Men Are From Mars, Women Are From Venus.

“Online dating takes effort, and effort equals time.”

“Online dating takes effort, and effort equals time,” he continued. “With [dating apps’] explosion in popularity, it means that you have a huge dating pool at your fingertips, but you’re also in direct competition with everyone else in your area. So if you want to have a chance at meeting your most intriguing matches, you need to have the best possible profile, photos, and messages.”

In my guise as a middle-aged American male, it’s my job to pursue women on our clients’ behalf. These people are often in their early 20s; young women with less dating savvy are easy targets for the company’s methods. “Rule 1: Don’t make her think too hard,” the manual says. “When writing sales copy…the goal is to reduce her ‘cognitive load’ so she’s more likely to reach the end and still have energy to write out a reply.”

What does a “low cognitive load” pick-up line look like? My personal favorite:

A beautiful seaplane. A suitcase full of cash. And a dashing co-pilot. Whereto?

These pick-up lines are mostly sent by a third type of employee, “Matchmakers,” who send out opening messages en masse across every dating platform imaginable: Tinder, Bumble, match.com, POF, Luxy, and Seeking Arrangement, to name just a few. As part of the company’s all-inclusive service, Matchmakers will scour these platforms for potential matches and then send copy-and pasted opening messages to those who fulfill their clients’ preferences, such as “must love cats” or “should know how to cook.”

But combing through each woman’s profile would require too much time, so Matchmakers are instead taught to generalize a client’s preferences as much as possible and then select an opening line that could work for hundreds of women. For example, does Client X like to travel? That’s easy: Client X’s Matchmaker can search the company manual for the word “travel” and select from a handful of vague travel-related greetings. From there, after the client has approved the message, a one-liner blitz will rain down on dozens of dating sites, targeting hundreds of women with the word “travel” in their profiles.

“We have a lot of ice-breaker messages that are billed around specific interests, like yoga or skiing or having a very short profile,” Valdez told Quartz. ”If there’s a message that the client doesn’t like, we take it out of rotation.” After the Matchmakers have made contact, the Closers then step in to keep up the flirty banter and, hopefully, get their client a date. Clients are sent weekly emails to alert them of numbers we’ve scored or, for Platinum clients, when and where to go for a date we’ve arranged.

This messaging “blast” technique may appear lucrative compared to the average neighborhood yenta, but it has occurred to me that good matchmaking may not be in the company’s financial interest. When a client pairs up, they leave the service. And with ViDA charging each client anywhere from $495 to $1,695 a month for its services, there is a significant financial incentive to keep them coming back.

So, tell me about yourself

Originally a sales guy with no time for “real dates,” Valdez grew ViDA’s brand out of his own experiences in the dating world. Before Tinder normalized “DTF” (“Down To Fuck”) as an opening salute, Valdez would send copy-and-pasted pick-up lines to dozens of women a day and track their effectiveness on spreadsheets. “Online dating is a numbers game,” he would write in the ViDA training manual years later.

His idea for a digital-dating-assistant service started in 2009, when he was frustrated with the amount of time it took to search for matches online. “I was working 60 to 70 hours a week and simply didn’t have time to keep up with online dating,” he said. “Before my life had gotten so crazy, I’d managed to develop some material that worked really well on the dating sites I was using. But I was at the point where I was only able to return messages sporadically, which obviously didn’t go too well with the matches I was interested in.”

“I thought, ‘Why couldn’t I just take what I had developed, and train someone else to sound like me, and outsource my online dating to him?’”

“I found myself wishing there were two of me,” he continued. “I thought, ‘Why couldn’t I just take what I had developed, and train someone else to sound like me, and outsource my online dating to him?’” After finding someone on Craigslist who “did a really great job,” Valdez started thinking about how many people were in the same position: time-poor professionals who might benefit from some of the lessons he’d learnt. “If it weren’t for my relentless dedication to cracking the code to meeting and attracting the right person, I probably wouldn’t have met the girl I’m with now.”

Today the company employs 80 people and boasts 2,500 “satisfied customers.” But the same cannot be said for all of its employees.

I asked my coworkers how they handle the moral flexibility that the work demands. One male Closer told me that it felt rewarding to “help men too old to understand the internet,” and that “some people are too busy for all that.” Another writer told me that “finding love is a mysterious process, so we use data.”

The service’s data-driven approach to professional flirting became clear to me during my training. “We’ve discovered that a surprisingly large portion of the online dating process can be systematized into what is essentially clerical work,” read one line in my training manual. “Really, when you think about it, you’re writing sales copy.”

To this end, every message I send is logged into an automated system that analyzes response rates. Closers regularly discuss what works and what doesn’t, swapping tips in extensive email chains. There are required monthly team meetings, in which Closers help workshop opening messages and pitch new ideas. While the list of company-approved opening lines is constantly evolving, the formula is almost always the same: a vague reference to something on the match’s profile, followed by an extremely easy question, like “I see you’re into yoga…. so answer this question once and for all: which is better, hot or not?”

Paradoxically, ViDA’s manual says that honesty is key to seduction. One chapter titled Don’t Lie includes lines like, “There are few things women hate more than insincerity” and “If you’ve told your date you’re a six-foot-tall astronaut when actually you’re 5 ft 9 and sell insurance, she’s going to find out.”

“It’s about trust and making sure we represent them in a way that’s comfortable for them and feels authentic, because at the end of the day they’re going to be the one going on the date,” he added over the phone. “It’s important that everything that we do feels right and feels true to who they are.”

But I’m not an astronaut or an insurance salesman. I’m a woman sitting in my living room in Montréal, running proxies on my smartphone and laptop. I’m logged into my client’s Tinder and match.com accounts, appearing on these platforms (with the help of numerous fake GPS services) to be the man I’m pretending to be. I sit on my couch and wait for messages to arrive in their inbox.

“Oh, you like Pink Floyd?” I write to one match. “Cool. I saw them in concert in ‘77.” This technically isn’t a fib: My client did see Pink Floyd in 1977—though I wasn’t born until 1992.

I was three weeks into my contract when I encountered a client whose age was listed as 25. Written beside his photos was a casual disclaimer: “…he’s actually 33 but wants to present like 25 to attract younger ladies.” Shaving two or three years off of a client’s age was common practice, but eight years felt predatory. I sent an email inquiring about the company’s policies, and never heard back.

“If a client requests it, we may add an inch or two onto the displayed height or shave a year or two off the listed age, but we don’t like to do anything that’s really big,” Valdez explained to Quartz. “The goal is for the client to meet their matches face to face and hopefully spark a long-term relationship. So big lies about important facts undermine that goal. We make sure our clients understand that.”

If a woman doesn’t respond to our cheesy pick-up lines or cough up her number by the third message, I’m instructed to move on, as the match is no longer cost-effective.

Despite my attempts at embracing the “Alpha Male” attitude, the training staff have repeatedly told me that my writing is “too female,” a characteristic that has never been fully explained. To mitigate this “error,” I’ve been told I need to use shorter sentences, ask fewer questions, use fewer smileys, wait longer to reply, and set up dates before even asking if the woman is interested. If a woman doesn’t respond to our cheesy pick-up lines or cough up her number by the third message, I’m instructed to move on, as the match is no longer cost-effective.

Closers aren’t paid for the time they spend waiting for new messages, so I reread my clients’ intake questionnaires in order to bill my base salary of $12 an hour. Every client must answer 50 or so questions about themselves when they first sign up and go through a 90-minute interview, supplying Profile Writers and Closers with nuggets of mundane information. Most of it is useless when it comes to fuel for flirtatious banter—like “I took piano lessons until I was 5 years old,” or “I had fun at my sister’s wedding”—but these lifeless anecdotes are all we have to draw from.

Several times a day, female staffers receive Photo Ranking Requests, in which we rank new clients’ photos in order of attractiveness. This helps Matchmakers select which photos to use when building or updating a client’s dating profile. “We don’t like to declare that this client’s a 9, this client’s a 6, or compare our clients in any way,” Valdez said. “We do, however, rank the attractiveness of a single client’s photos against one another. We just employ a data-driven ranking process for choosing the most attractive pictures…We do this internally to determine a client’s optimal photo lineup.” He mentioned that OkCupid used to run a similar service, and Tinder can also optimize your photographs so that the most popular are shown first.

One Profile Writer I spoke with (I’ll call him Doug) was candid about his dilemmas over the company’s practices. After working as a Closer for two years, Doug had asked to switch to Profile Writing. He’d taken to referring to Closer work as “the dark side.”

Doug told me that a lot of clients never call the women “who have been really engaged emotionally and are responding to our messages.” Once Closers receive their commission for getting a number ($1.75 each), they move on. But if a woman never hears from the client—the man she believes she’s been corresponding with the whole time—she might send more messages through the app, upset that she hasn’t heard from him. But the Closer is no longer allowed to reply, so he ghosts her. There’s no more money to be made.

“I am creating these bitter women out there,” he said. “I ask myself if I’m part of the problem.”

Doug learned to unmatch from women once he’d received his commission. It was easier for him that way.

Fool’s gold

What kind of person would pay strangers to score them dates online, and then not even bother to call? Clients who can afford to ignore phone numbers because they receive so many a week are internally referred to as “Cash Cows.” They go on several dates a week for months or sometimes years on end, traveling frequently to new areas and an ever-expanding pool of women. These clients tend to be younger men in high-powered finance jobs.

Valdez said that the typical client profile tends to be somebody between the ages of about 28 and 52, with most being in their 30s. (He also claims that one third of their clients are female.) From there, it divides into two camps: those who “have more money than time,” and those who are just plain frustrated. “Entrepreneurs, doctors, lawyers,” he lists. “Programmers, too—especially programmers in the Bay Area. We get a lot of them.”

“[ViDA allows] them to delegate this particular aspect of their lives to an expert, just as many have financial planners, landscapers, personal trainers, and mechanics on speed dial.”

These types of professionals are money rich but time poor, he explains. Valdez referenced a recent survey that shows online love seekers are spending 10 hours a week on dating sites and apps. “Our clients have successful careers,” he said. “They work, they travel often, and they just don’t have that time. So the need a company like ViDA fills is allowing them to delegate this particular aspect of their lives to an expert, just as many have financial planners, landscapers, personal trainers, and mechanics on speed dial.”

Indeed, there are plenty of older men seeking age-appropriate, long-term relationships online. These are the types of clients Doug and Valdez always refer to when justifying the service, as our work helps them navigate unfamiliar territory. After all, internet culture does not come naturally to some, and many of our clients are widowed or divorced retirees.

I asked one of my trainers if the company takes on any married clients. Men looking to quietly set up extramarital affairs would benefit from the company’s all-hands approach; they wouldn’t even need to install the dating apps or visit the websites we use. Matchmakers will select their best photos, Profile Writers will make them sound appealing, and Closers will do all the flirting for them. Our clients need only check whatever email they’ve provided for date locations and phone numbers.

My trainer was quick to reassure me that they refuse those prospective clients. “Even if the guy’s lying about it, Scott has a whole system for how we deal with that situation.”

When asked about this policy directly, Valdez pointed out that their website clearly states that they do not take on married clients or those looking to cheat; he also said that the extensive on-boarding process tends to weed out any immoral actors. “I couldn’t sleep well at night knowing we are helping people wreck their families. We’ve never knowingly helped cheaters,” he says. “There are a lot of other ways I’d prefer to make money than helping people mess up their family.”

Is it even legal?

The company’s practices may be unethical—but they’re not illegal. Once the company obtains the client’s permission to impersonate them online, there are no laws against what Closers do.

Instead, it’s left to individual platforms to crack down on fake accounts. OKCupid, for instance, makes it clear in their terms of service that third parties are not allowed to open accounts, and it’s not uncommon for clients’ profiles to get flagged and deleted. But from a legal perspective, unless a Closer harasses or threatens a match, exposes a client’s confidential information, or asks for money, everything they do is legal according to US, Canadian, and UK law.

But legality aside, these cut-and-paste flirtations perpetuate negative gender stereotypes, and they reinforce an oversimplified (and destructive) view of romantic expectations.

Men and women on online-dating platforms therefore learn to emulate personalities that yield quantifiable results.

As dating platforms become flooded with calculated, flirtatious spam, men and women on these sites learn to emulate personalities that yield quantifiable results. This means playing down unique traits and unorthodox views to the point where a total stranger—like me—could literally do it in their place. By trying to appeal to dozens, if not hundreds, of strangers at the same time, we forfeit our ability to take risks and experiment with social norms; only placing safe bets robs us of new and genuine experiences.

But the steepest price of this online anonymity appears to be human decency, which—as I’m often reminded at ViDA—doesn’t lead to dates.

For example, one match told me that she’d just put down her family dog. Still in training, I wasn’t sure what to do. I wrote out an apology for her loss and sent it to my instructor for approval. He crossed out my response and wrote underneath: “Alpha Males don’t apologize.” What we sent back instead was an upbeat story about our client’s two dogs, which was a shamefully inconsiderate reply in my view. I expected to never hear back from her, but three exchanges later, she was sending me her phone number.

It was my first commission: $1.75.

Had she blamed my client’s callous response on internet miscommunication? Or was she learning—just as I was—that reaching out for a unique connection online would lead only to awkwardness and rejection? Every time she has an interaction in which her feelings are ignored—whether it’s online or in-person—I worry that she’ll learn not to talk about her emotional needs, or any needs of any kind.

As the disillusioned masses learn to offer less and expect nothing, companies like these can take advantage of this extraordinarily low barrier to entry. That cringe-worthy “dashing co-pilot” opening line might sound impossibly lame—but it works. (And at least it’s not the bare minimum “DTF?” or an unsolicited dick pic.) As a result, businesses such as these are an economic inevitability.

*   *   *

I was given my first female client after two months with the company. Women seeking out our services require a very different approach. When talking to my new client’s matches, I was told to make her voice sound “feminine (soft, warm, delicious, flowing, focusing on how she feels about things).” I had to “focus less on her career and more on her outside life…write longer sentences, more emoticons, and be more playful.”

In Doug’s view, it’s our job to act as gatekeepers for these female clients—to make sure no subpar matches make it through. “Women are so put into a box, and they aren’t going to represent what they really want,” he said. According to him, a Closer should ask the tough questions that female clients aren’t comfortable asking themselves: Does the match want children? Are they looking for something serious? Are they dating anyone else right now?

I took his advice to heart and played hardball with my female client’s matches. None of the men fit her description of what she wanted, so by the end of the first week, I had not pursued any phone numbers. I was reprimanded for not producing results, and for wasting both the company and the client’s time.

“Our clients are interested in finding their ideal match, and if the writers aren’t getting them closer to that goal, then we’re not fulfilling our commitment to our customer,” Valdez said. “So we might realize that a writer’s writing style isn’t a fit for a client or the match that client wants to attract, so we simply shift them to a client that he or she is better equipped to help.”

Another Closer was given my account. Overnight, they scored seven numbers from the matches I’d already vetoed—an additional $12.25 in their pocket.

I decided to make my exit soon after.

My initial curiosity about these dating assistants had morphed steadily into deep disgust: with the company, with Valdez and his manual, and—above all—myself. The sight of my first paycheck sent me crawling back to bed in a guilt-ridden panic.

I grew suspicious of my own dating accounts—not just of the men I matched with, but of my own ability to present a likable version of myself online. Every new conversation felt like a minefield, filling me with equal parts boredom and dread. To my dismay, I started to want my own virtual dating assistant.

This all begs the question: Have you unknowingly flirted with a professional Closer? Me, even?

As we grow accustomed to foisting more and more complicated emotional tasks onto digital butlers, we lose our ability to tolerate inelegance or find value in social failure. Moments of awkwardness and heartbreak are an inevitable part of the dating experience, and they are essential in our evolution into mature adults. By outsourcing our courtship to robots (and robot-like humans) we might save ourselves some pain in the short term, but it degrades us, simplifies us, and fails to provide for our ultimate goal of finding someone accepting of our flaws. In this age of automation, romance isn’t just one click away—it’s guaranteed.

But if you’re willing to scrape the bottom of the barrel, what isn’t?

Follow Chloe on Twitter. Learn how to write for Quartz Ideas. We welcome your comments at ideas@qz.com.

Note: This piece was updated with a more recent opening line currently in rotation that is sent by Matchmakers.