From DMs to Dinner: The Messages That Closed the Gap

About a year ago, I was talking to a buddy of mine over drinks about the absolute horror that is online dating. And at that time, I was just about ready to throw in the towel. Alright, fine, what I really wanted to do was throw my laptop into the ocean. I just wasn’t getting results on any platforms, even though I was paying for the higher-tier subscriptions. The few times that I felt like I was getting responses turned out to be bots. And the even fewer times that I felt like I actually connected with a real human, they would ghost me before ever seeing me in person.

But I realized that the more I railed against the woes of online dating to this friend, the quieter he became. Finally, I realized what was going on.

“Wait,” I said, “You’re actually getting dates out of this, aren’t you?”

He gave me kind of a shy shrug and said, “Yeah, I’ve been doing okay.”

I asked him what he could possibly be doing to have more success. I mean, I wasn’t going to say it out loud, but it’s not like this friend was more attractive than me. And to be perfectly frank, he wasn’t as well off as I was, either. There had to be something else going on here.

Finally, he asked me to see my interactions with women in my DMs. Maybe there was something there that I wasn’t seeing. And with another blow to my ego, my friend got quiet again.

“What?” I asked, starting to actually panic now. “What’s wrong with my DMs?”

He hesitated and then said, “Look, I’m just going to be honest. I wouldn’t want to meet you in person either. You come off like a total jerk.” Only, he didn’t say jerk.

True, my ego was hurt. But I asked him for advice on how to make my conversations more palatable to my audience. Here are the messages that he suggested I include to move from the DMs to first dates:

I noticed _____ on your profile, and I have so many follow-up questions!

Basically, the first thing that my buddy suggested I do was to stop talking about myself and start being more curious about her. I guess, coming from a sales background, I had been treating my DMs like a sales pitch, trying to convince women why they should date me. But really, this buddy said, I should be getting them to open up about themselves.

So, I started practicing sending messages like:

• “I see from your profile that you’re into horseback riding. How did you first start getting involved with that? What’s your favorite ride you’ve ever been on?”
• “Is that your dog in your profile picture? What’s their name? Do you have other pets?

Okay, maybe it seems really basic, like duh, I should have been asking questions about the other person. But I was really shocked at just how much more receptive women were when they felt like I wasn’t just trying to get something from them but actually interested in learning about them.

I saw on your profile that you like ______. I’ve always wanted to try that. Would you be my date?

Sure, basic conversation is important, but my buddy said that I would also need to move the chat offline. And, his suggestion for doing so was to make sure she knew I would be willing to do something that she also wanted to do. A few ways that I used this script included messages like:

• “Moment of vulnerability: I’ve never tried sushi. But I see you eating it in your profile picture. Would you be willing to watch me make a fool of myself trying to figure out chopsticks?”
• “I see that you’re a big reader. It was actually on my list of goals this year to read more. What do you think about meeting up for coffee and a trip to the bookstore?”

My friend stressed that the important part was tailoring my message to something she had in her profile. That was the way that I could show that I pay attention to details and am willing to try something new.

It’s so exciting to meet someone who also loves ______. Maybe we can go together sometime?

Shared interests are another way to build a connection, or so my buddy suggested. He told me to find something that we had in common, chat about it briefly, and then build a date around it. Here’s what it looked like in practice:

• “Okay, marathoner! Tell me about your last race! Do you have anything coming up? I have a half in about two months, I’d love a running partner.”
• “So I take it that you’re a movie lover too? What’s something you watched recently that you can’t stop thinking about? Also, I know there’s a film festival coming up, and I’d love to go with a fellow movie buff.”

This was one of the most successful ways I found to connect with people on dating sites. I mean, we all want to find someone who understands our passion, right? It also made my first dates a lot more engaging. I was able to think more creatively than just “let’s grab drinks” or “let’s meet over coffee.” And women really seemed to respond to that.

Other tips I used to improve my DM skills

As I started to have more success with chatting online, there were a few takeaways that I can point to and say, “Yes, that was the secret sauce!” Here are the most important:

• The “hook” is a human connection. There’s no universal script that you can use with every person, and cookie-cutter messages are likely to turn people off. So, you have to dig a little bit and find the thing that connects the two of you!
• Curiosity is key. I’m not just saying this so that you can trick someone into wanting to date you by asking a few questions to feign interest. What I mean is that becoming a more curious person makes you more dateable. Curious people are interesting and fun to be around. Sure, it takes more mental energy, but it also makes dating and life in general more fun.
• Take ghosting personally, but not in the way you think. I’m not suggesting that you be so hard on yourself when someone ghosts you that you think about giving up on online dating altogether. What I mean is that after you’ve been ghosted, do a little bit of a review of the conversation, and think about it from the other person’s perspective. If you were in their position, would you want to date yourself? Would you find the conversation engaging? If yes, then congratulations, it likely wasn’t something that you did wrong. Remember that people are typically dealing with their own fears, insecurities, and barriers that have nothing to do with you. But if the answer is no, you can use that information to make your next chat more engaging.

Feeling trapped in the DMs can be exhausting and even a little bit demoralizing. But it doesn’t have to be your only experience with online dating. Once I put my buddy’s strategy into practice, I was amazed at how many more dates I had lined up. And now, I get to be the guy who gives a shy (albeit smug) smile when someone asks me if online dating has been successful for me. Because, ever since making a few changes, my inbox has really been full!