How do you move from matching on a dating app, to texting, to a first date?


Let’s take a little break from dating and relationship advice that deals with the tough issues, and let’s just talk about actually getting on a date after matching on a dating app. Chances are good that if you’re reading this, you’re on at least one dating app. Chances are also good that the whole online dating process doesn’t feel natural. Dating norms are incredibly varied to begin with, once you add in an online element, all bets are off. Just think about the way we communicate and get to know people on dating apps and how vastly different it is compared to meeting people in real life. There is no swipe right in the real world, at least not that I’m aware of, but even things like opening conversations look very differently when you compare online dating to offline dating. You’d never approach someone at a bar and ask them how their week was, you know?

It’s perfectly okay to not be knowledgeable about online dating customs, because if we’re being honest, they don’t really exist outside of basic norms around decency, which are largely ignored. If we ever do come to an accepted consensus on what’s an online dating norm, they’ll eventually grow and evolve in the same way that offline dating customs grow and evolve year after year. And that’s usually a good thing. Personally, I’m a big fan of the fact that I don’t need to provide oxen as a bride price, because I’d be at a loss as to where to even get live oxen in New York City. (I’m kidding, I’ve got a guy who works at a vivero that can get you live oxen if you give him a day or two heads up). In all seriousness, people’s unfamiliarity with how things should progress in dating is completely understandable, even more so with online dating. Which brings us to getting an offline date.

Most people on dating apps share a common goal: To go on a date. Sadly, many people are clueless about the best way to get your online crush on an offline date. Luckily, I know a thing or two about transition from a dating app, to texting, to a first date. It’s not rocket science, and honestly, the hardest part is getting people to even respond to you once you’ve matched. Once you’ve done that, it’s a lot easier than you might think to transition offline. So, here’s how I do it. I think this approach would work for you too:

Transitioning from the Dating app

This part of the post is going to make three assumptions. First, that anyone regardless of their gender or sexual orientation can and should initiate transitioning from a dating app or website to another mode of communication. Don’t wait for them to initiate because of some outdated (probably gendered) rule, fortune favors the bold. Second, let’s assume that you want to transition from a dating app to communicating by telephone prior to a date. If you don’t want to do that, the advice still applies for the most part, just do all the steps on the app itself. If you do want to transition from a dating app to, let’s say email, this advice applies too, just swap out “phone” for “email address”. Third, let’s assume that your goal here is to go on a date with a potential for future romance, and not a quick hookup or to make a new friend. Some of the advice might apply for both of these scenarios, but a lot of it won’t. If you want specific advice for transitioning offline when your goal is hooking up, making friends, or something else, you can always email me or DM me on Twitter.

With that out of the way, here’s how your transition from a dating app to communicating by phone:

  1. Establish attraction and screen them. In those first few messages, your goal should be to try to get a read on the person you’re messaging. If you get a bad read on a person, trust your instincts. Whatever initially attracted you to their profile and their pictures, now’s the time to confirm that attraction and build on it. Or, figure out if you read them completely wrong. You’ve probably got some immediate deal-breakers, so now is the time to figure out if they make the cut. Also, make sure that you clear their deal-breakers. I’ve been on a few dates with women who, only while on the date, revealed that something about me was a deal-breaker, whether that was religion, my ethnicity, education, or career. Besides that, just try to establish a basic comfort level when communicating with them. If they can’t hold a conversation with you over a dating app, odds are good that they won’t be able to have one with you over text*.
  2. Make sure your conversation is progressing. There are lots of people out there who will message you after matching, and keep responding to your messages, with no real desire to ever actually meet you. Take for example the bizarre exchange between Michael Che and Leah McSweeney. Opinions on his texting etiquette, or her saying that some men “look gay” as a pejorative aside, their conversations can tell you a lot. Che responds to McSweeney even though I’m sure that at least after the first exchange, he’d already decided that he wasn’t going to meet her. (Probably because she’s the sort of garbage human who uses “gay” as a pejorative). If your conversations on dating apps seem to have the same sort of feel as the conversation in that article, with lots of back and forth that doesn’t seem to progress, transitioning to texting might be pointless. If your conversation seems to build in a coherent way, consider transitioning to texting. If you’re unclear on what conversation progression looks like so here’s a basic idea of what a conversation that progresses looks like:  You mention a topic. You both talk about that topic using more than just one word answers. You ask about something related. You both talk about that topic using more than just one word answers. Rinse and repeat.
  3. Hint at a date, offer to exchange numbers. After you’ve done all the hard work, now it’s time to pull the trigger. Asking for someone’s number while also floating a very rough draft of a date idea is something that I’ve found works really well. It can be as simple as saying “Hey, remember when you mentioned that you love whiskey? Well I know a bar that has an awesome selection, and I’d love to take you. Want to plan a date over text?”. There is always the risk that whenever you ask, whether it’s after one day or one week of texting, they might consider it “too soon” to exchange numbers. As I mentioned before, no set dating norms for online dating means everyone has their own idea of what is “too soon”. If you feel like you’ve done a good job of screening someone, and think you want to move to date planning within the first day or two of messaging, go ahead and ask to exchange numbers. On average, it usually takes me somewhere between 2-5 days of messaging, or about 5-10 or so conversation smaller conversations to get to this point.If you’ve been messaging for a month without exchanging numbers, you should consider that a warning sign that they might not want to meet you. I’m not saying that you need to meet within a month, but in my experience someone who isn’t ready to even start the discussion on meeting within 30 days of messaging is likely to not be serious about meeting.

*There will be exceptions, because some folks are bad at texting. If they tell you this, your transition to the phone should probably be geared toward calling them. If they’re bad on the phone as well, they might just be bad at communicating with you.

Transitioning to meeting in person

Okay, so you’ve done your pre-screening, and you’ve decided, screw it, they seem fairly not murder-y, might as well exchange numbers. At this point your focus really should move toward date planning. Here’s how to do that:

  1. Preparation. At this point, build on the conversations you’ve already had, and the one where you floated a date idea and start figuring out when you’ll meet and what you’ll be doing. This is another area where people’s ideas of what’s a dating norm differ drastically. A lot of the time, you’re proposed date idea doesn’t actually work for your first date, and you may get push-back for the activity you suggest. I’ve had potential dates shot down because someone thought the idea of getting drinks on a date was too cliché, and I’ve also had people shoot down really cool and innovative date ideas. My advice is propose a date you’ll feel comfortable with, and if they don’t like the idea, have another idea ready, or ask for a suggestion. Personally, I’m of the mind that if I come up with an idea for a date, and someone doesn’t like it, they should collaborate with me to come up with an idea they’ll enjoy, and not keep sending me back to the drawing board with no feedback. But, I’m not one of those people who thinks it’s ALWAYS up to the straight man to do all the heavy lifting for date planning. So, your results will vary. Ask them when they’re available, float a date idea and build from there.
  2. Confirm your date. Chances are good that there are probably a couple of days between when you get their number, when you start planning your date, and when you’ll be going on your date. If you’re date is the next day, confirm your date at the end of your conversation. If it’s 2 days or more between date planning and the day of the date, send a confirmation text on the day of your date, preferably in the morning, so that they know plans are still on. People are flaky as hell these days, and I’m willing to bet that many of you reading this have been cancelled on within an honor or two of a date. The best way to put people at ease, and make sure you don’t show up to a date that they thought was cancelled because you never reached out, is to reach out and confirm your date the day of your date. Doing this will serve a few purpose. First, it’s a confirmation, Second, a reminder, and Third, a chance for them to back of the date as early as possible so you have an opportunity to make alternate plans. Don’t send a text saying “Just confirming our plans tonight”, do send a text that says “Hey, looking forward to seeing you later at {Date Venue}”.
  3. SHOW. UP. TO. YOUR. DATE. You don’t need me to explain this, do you? In the rare instance where you can’t show up for a date, but you are legitimately interested in rescheduling, reach out to them as soon as possible, apologize for the inconvenience, stress that it’s a serious issue and you want to reschedule, and have a date already pre-planned to show that you’re serious.

Now, all you have to do is show up and be as charming and witty as you were on the app and over text. It should be no sweat.

Good Luck Out There.

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