Online Dating

Online Dating 101: 7 Steps to Writing a Standout First Message

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We got a plea from a male reader yesterday, who’s having trouble making his online dating messages stand out.

So girls and guys must have drastically different experiences with online dating. The girls post a profile and get bombarded with messages from guys, guys scan profiles and message the girls. So, do you have any advice for how to get my message to stand out? Or to just get a response?” -Daniel, San Diego

Okay, Daniel, here’s some advice.

1) Message her, don’t “wink” or “intrigue” her.

Most dating sites have a flirty option which allows you to express your interest without having to actually message a person. (On HowAboutWe, this is the “I’m Intrigued” button, on OKCupid it’s a wink.)

In general, this is not a good way for a guy to approach a girl on an online dating site. It says “Hey, I might be sort of interested in you, but I’m going to let you do all the legwork.”

Don’t give her a nudge and expect her to then message you, because she probably won’t.

2) Keep it casual and short.

This isn’t a cover letter for a job application; there’s really no need to be formal. Girls on online dating sites really can get bombarded with messages, and at that point, they’re not really likely to spend more than 15 seconds quickly scanning through a message before decided to keep reading or not, so keep it brief.

Try and keep the exact same tone you’d have if you were meeting her at, say, a party, rather than online. Polite, friendly, but casual. A message that reads:

“Hello, nice to “meet” you, I’m John. I’ve read your profile, and I think you sound nice…”

…is way less engaging than this:

“What!! You like Sports Night but not the West Wing?! I’m appalled. What’s your argument?”

Later, once you guys have gone back and forth a few times, you can feel free to write longer, more involved messages.

3) Don’t start with “I think you’re very pretty.”

You might think it’s flattering, but in general women don’t like to be approached like that. Especially online, when women maybe a little more on-guard, opening with a comment on their physical appearance runs the risk of seeming shallow and off-putting.

Besides — if they really are that pretty they’re probably hearing that from every unoriginal guy on the site, and it won’t help your message stand out. Start with something else, and then tell her you think she’s pretty when you finally meet in person.

4) Don’t make it about you.

Sometimes, misguided men will send out first messages that read like autobiographies.

“I studied architecture in college and studied abroad in Spain for a semester. My perfect night in involves a bottle of wine and my Arrested Development DVDs. I don’t smoke, but don’t mind if you do…Well, message me if you want to go out.”

Messages like this are not only boring (if she wants to know about you she’ll either click on your profile or, even better, ask you), but they give no indication of why you want to go out with her. Why should she bother to respond?

Try something like this instead:

“Whoa, you studied abroad in Ghana? That sounds amazing. Did you stay with a host family or your own place? I’d love to go to Africa some day.”

5) Prove that you’ve read her profile.

Online dating can seem scary and anonymous, which is why it’s so important to personalize your messages as much as possible. In your messages, you should make it clear that you want to go out with this particular girl, and that you’re not just sending a carbon copy out to anyone with breasts and a pulse in your zipcode.

Mention something specific in her profile. What is it about her (aside from her photo) that really caught your eye? Elaborate on that.

6) Funny is always better.

If your message can make a woman laugh (and with you, not at you), you’re already half-way there. Once she laughs, she lets her guard-down a little, she thinks you’re funny, and probably smart. Not that you have to turn into Seth Rogen all of the sudden, but in general, on the internet, humor is far less abrasive than, say, ardent fervor.

In other words, don’t be creepy! Don’t come on too strong! Women are extra sensitive to this online.

Related: Online Dating 101: Sending a Second Message

7) Give her something to respond to.

After you’ve composed your message, ask yourself what you would respond if you received this from someone. Did you ask her a question, did you set-up a joke she could build on?

And, if you’re on a site like HowAboutWe, and you’re responding to a specific date idea, please know that it’s not really enough to just write back “I like your date idea, let’s do it.” Most girls require a little more small talk before committing to meet someone in real life.

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