How To Win At Online Dating

Illustrated by Emily Turner.
Even those lucky few who have been in long-term relationships since before the dawn of Tinder probably know that online dating isn't exactly a walk in the park. Ignoring unsolicited dick pics and otherwise inappropriate behavior, online dating is nerve-wracking because, well, dating is nerve-wracking. And trying to find dates online gives you way more time and opportunity to obsess over everything you say and what you look like.
So we talked to Joshua P0mpey, a matchmaker and founder of Next Evolution Matchmaking to learn how to craft the perfect profile. "If you write your profile and create your photo gallery correctly, no one should wonder if they want to message you. They should feel as if they need to message you," he says.
Ahead, read Pompey's tips on everything from what to write and what pictures to choose to what to say in your first message.
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illustrated by Tristan Offit.
Before you even open the app...

Plenty of people agonize over what to write on their dating profiles — which jokes are witty enough, how deep should they get into their career info, and is their pickle obsession quirky or cute? And that's why Pompey suggests "interviewing" yourself before you sit down to write the profile. "The best online dating profiles are able to give the reader a strong sense of where that person has been and where that person is going in life and what they're like now," he says. Trying to write a profile that encompasses all of that on the fly is really difficult, so brainstorm first. Ask yourself what you're most proud of, what interests and hobbies are really important to you, what your dreams are, and what you are looking for in a partner. Being able to answer those questions for yourself will result in a more coherent and comprehensive profile.
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illustrated by Tristan Offit.
When you're writing the profile...

Break it up: The structure of your profile is very important, Pompey says. "People have very quick attention spans, so break your profile into two to three sentence mini-paragraphs at most," he says. Online daters tend to skim profiles for information at first and then go back to read the whole thing if they're interested. So having short paragraphs — maybe one dedicated to your hobbies, one to your career, and one to where you want to travel — makes it easier to skim.

Be conversational: If you can write your profile almost as if you're speaking directly to the people who are reading it, that will make it feel as if they're really getting to know you, Pompey says.

Open with an attention grabber: "The beginning of the profile is your chance to instantly draw someone into who you are and what you're all about," Pompey says. So lead with something unique or interesting about you (bonus points if it's funny).

Add "profile bait": What Pompey calls "profile bait" is anything that makes it easier for the people reading your profile to think of an opening line when they message you. "So if I've been talking about traveling, I might say at the end of that sentence, 'Where's on your bucket list these days?' and that baits the reader into starting the conversation," he says.

Write with words of confidence: "A lot of people accidentally use language that makes them appear needy or a desperate or seem like they're disgruntled," Pompey says. For example, writing something like "I hope to meet someone who's intelligent, ambitious, and fun" seems totally fine. But the word "hope" is passive. It's better to write, "The perfect guy for me would be intelligent, fun...," he says, because it's more assertive. In general, be positive. List what you want in a partner and avoid self-deprecating jokes.
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illustrated by Tristan Offit.
When you're choosing photos...

Every photo you post is an opportunity to tell a story about yourself, Pompey says. So make sure the story is interesting, and choose a wide range of photos. Rather than posting five selfies, choose a photo where you're out with friends, one from when you were on vacation in India, one from the animal shelter where you volunteer, one from your brother's wedding, and one from your favorite beach (a selfie or two in the mix won't hurt, either). "The more stories that you can tell with photos, the more you'll be able to visually depict what it's like to be in a relationship with you and the more powerful your photo gallery will be," Pompey says.
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illustrated by Tristan Offit.
When you're sending a first message...

Anyone who's spent even a few weeks on online dating apps knows that it can get really monotonous after a while, so it's important to avoid generic opening lines like, "hey there."

"Always come in with something that's at the minimum a little bit playful," Pompey says. Scan the person's profile for something you have in common, he says, and lead with that. Then, always end your message with a question.

"If you can't find a super strong commonality, ask what they're most interested in or passionate about," Pompey says. "Because at the end of the day, most psychology shows that everybody's favorite subject tends to be themselves."

Remember that you always want to make it easy for people to respond. Most people look at their online dating messages when they're on the go after work, Pompey says. So you want to ask interesting questions, but you also don't want to overwhelm them. "While asking 'What's the most adventurous thing you've ever done in your life?' might seem like a great question, it requires someone to scan the entire duration of their life," Pompey says. Your match could easily get distracted or put the phone down and forget to look back at the message. "Whereas if you asked 'What's something adventurous you'd like to do going forward?' it's a much easier, low-stakes question that doesn't involve as much thinking," he says.
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illustrated by Tristan Offit.
When you're responding to messages...

After you've either sent or received the first message, it can be easy to fall into the trap of wanting to type out your whole life story. Don't. Remember that people have short attention spans and are also often answering messages on the go. So a long, winding message will likely get lost in hustle. "Be as economical and as efficient with your words as possible, in a way that still maintains interest and shows that you are interested in the conversation," Pompey says. And don't stop asking questions — it's the easiest way to keep the conversation going.
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illustrated by Tristan Offit.
When you're setting up the date...

Some people can have a tendency to go back and forth on the dating app for weeks, but that's almost always a mistake, Pompey says. You and your match might seem meant-to-be on paper, but you can't really know if you'll hit it off until you meet face-to-face. So as long as you're both in town, set up a meeting after a few good back and forth messages.

"You want to get to a point where you just give the other person your number and say, 'Listen, you seem like one of the few people I'm interested in getting to know. Feel free to reach out,'" he says. And keep the time of week in mind. If you've been messaging from Tuesday through Thursday, you'll want to give your number out before the weekend starts, because your match might be busy with weekend plans and that's a long time to go without communicating.

Once you've given your number out, you and your match can move to text, but it shouldn't take much longer to plan an IRL date, Pompey says. Giving your number indicates that you really are interested, so it's time to see if you and this person have real chemistry.

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