Swipe Smart - Advanced Tips for Online Dating Success

You Matched with Someone Online - Here are Some Tips to Get You to That All Important First Date

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If you’ve followed me for a while, you will know that I generally do not favor online dating. (I have written a book called “Meeting People in Real Life,” after all.) However, from time to time, I do fire up the dating apps to see what they’re like. I do this to stay relevant but also because it seems like it’s where most people looking to date are. Also, I can only spend so much time each week hanging out in my grocery store and asking ladies for their secret tips on selecting a ripe avocado. (I really have learned everything there is to know about how to select the perfect avocado.)

I’ve been revisiting a few dating apps these past couple of weeks and enjoyed some dates. It got me thinking about some advanced tips that I could give to help people have more success. By “success,” I mean in a relatively short time connecting with and arranging an in-person date with a real live human being. What happens after you meet is up to you. However, in this article, I will aim to give you some tips that will help get you to the point of meeting up.

The advanced tips below come in handy after you have matched. If you are having trouble getting matches, it may be for a variety of reasons related to your photos, what you have written in your bio, or what platform you have chosen to date on. However, assuming you actively using a dating app and you are getting matches, here are my advanced tips that will help you to get out on dates.

Humor, Humor, Humor

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Consider that everyone is swamped with social media, email, and text messages. I just did a quick check of the two dating apps I’m using, and I have 21 messages that I need to reply to. It’s too much and going through replying to everyone feels like homework. I have asked several women how many messages they receive when they use dating apps, and I have gotten answers like dozens, hundreds, and one particularly attractive woman told me she had over… 2000. So, a simple “Hey, how ya doing?” will not be likely to get a response. Do you know how you get your message noticed and more likely to get a reply? Make the person you’re interested in laugh. If you can make someone laugh out loud at your cute message, that’s golden. But even just being clever enough to elicit a chuckle greatly increases your chance of getting noticed and then getting a response.

It’s hard to be funny when you don’t really know the other person. The way I manage this is to look for details in their photos and think carefully about what they say in their bios. This is usually enough for me to come up with a simple one or two-line quip. It’s important not to say anything that is mean or insulting. Just come up with a funny comment and aim to make the person laugh. Here are a couple of examples from my current round of online dating:

I messaged a woman wearing an “I ❤️ Tokyo” T-shirt in one of her pictures: “I’m thinking of going to Japan,want to come? Kidding! Going to Japan is more of a second date kind of thing…”

To a woman who wrote in her bio that she’s looking for someone “lovely, kind, and intelligent,” I wrote: “Lovely, kind, and intelligent… I could aspire to those. Plus being dangerously good at sending witty messages. 😉”

As you can see, in both cases, I looked carefully at what the other person was showing in their pictures or saying in their bio and turned it into a funny opener. Were they laugh-out-loud funny? Probably not. But the goal is to be funny enough to stand out and get noticed.

It’s Your Job to Move Things Forward

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A common trap is connecting with someone and sending several messages back and forth but you never get together and meet up. I call this the “texting buddy trap.” I consider this a trap because the point of online dating is to go… dating! If you message back and forth and never meet, then you have found a pen pal. So, every couple of messages, you need to suggest to the other person that you’d like to get together for a date. However, before you propose a meet-up, you must first build rapport. My technique here is to send one or two messages that are funny to establish rapport. Then, after two of these (never more than three), I suggest getting together for coffee (or going to Japan, but in most cases, it’s coffee). Now the person knows that I clearly want to go out with them and I’ve put an offer on the table that they can either accept or decline. If they accept, great, you have yourself a date and you can skip my next tip. But what if they decline?

It’s Always a Test

Often, when you propose a date, the other person will decline. In many cases, it’s not because they don’t like you. They’re simply busy and it’s bad timing. (Their grandma is sick, they need to wash their dog, they have an exam the next day, the reason they give doesn’t really matter.) What’s important is that you understand that this is a test. Based on how you answer, you will pass or fail. When the person declines and you lose your cool or respond in any way that is needy, you fail. By keeping your cool and responding in a non-needy way, you pass.

To be cool, you need to show that declining your offer to go out was not a big deal. If they say they can’t get together because they have to wash their dog, don’t even mention the date. Rather, message them back and ask about their dog. (Or anything else, do not mention they declined your date… you’re too cool to care!)

To be not needy, you must not propose another date right away. If the person can’t go out with you on Sunday and you message them back right away and say, “How about Monday!?” after then after they decline that offer, you reply with, “What about Tuesday!?” that is super needy. Cut that out. Send them a clever or funny message or two and build a little more rapport before suggesting another date. One thing I will do if I am having trouble arranging a date on a particular day is to ask the person when is good for them. Then, if they come back to me a day and time, I do what I can to make it work. However, I never start by suggesting that the other person picks the day and time for a date, rather, I use this more as a last resort. This is because leadership is attractive. Demonstrating your leadership and confidence by proposing the time and place for the date will be noticed and, in most cases, appreciated.

The ultimate non-needy move is to walk away. If your messaging and date proposals are not getting you anywhere, be prepared to move on to someone else. Occasionally, after I stopped messaging and moved on, the person noticed and reinitiated contact with me. In this case, I don’t waste any time, and I simply come back with another proposal for a date. In most cases, the other person will accept because you have already trained them that you are willing to walk away if they aren’t able to move things forward with you.

And if you do walk away and the other person never reinitiates contact, so what? At this point, you were never going to get together with them anyway, so you are better off for simply moving on.

There’s a Lot of Competition on Dating Apps

When I was in London, I went to several social meet ups. These events were packed with people, all of them well dressed, and many of them attractive. Even though everyone was there to meet people, because they were crowded and there was a lot of competition, it was actually quite hard to meet any one particular person. You had to put yourself forward and make a real effort to get the attention of anyone. Dating apps are very similar to this kind of environment. If you sit back and wait for the person you like to notice you, you may miss your chance. You’ve got to work at it. (I know, being funny with just a photo and a short bio is hard but it’s a skill you can get better at if you practice.) Remember, people are on dating apps to meet people! Getting that one special person to meet you can be tricky but by following my advanced tips above, you can greatly improve your chances.

If you are using dating apps as well, feel free to comment and share your experiences! I would love to hear them. In the meantime, happy dating!

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