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• Last updated: May 29, 2021

6 Tips for Successful & Gentlemanly Online Dating

Online dating phones connecting with hearts.

Editor’s note: This is a guest post from Jordan Zammit

Tell someone that you’ve dabbled in online dating and they might give you a look like they’re thinking about which letter of the alphabet would be most appropriate to give you in scarlet. But really, with the dawn of dating websites, Tinder, and the endless cycle of clones that come out almost daily, meeting someone from the internet is as common as meeting a stranger at a bar — at least for Generation Y.

So for those of us single folks who haven’t yet made the jump into this new internet trend (or have just dipped our toes in), here are a few ways you can give online dating a try while staying a gentleman.

1. Don’t Misrepresent Yourself

So maybe you were a football or track star in high school and now you’re a few years removed and about twenty pounds heavier — leave those varsity pictures where they belong (in a shoebox!), and upload something more recent. While meeting people and dating shouldn’t be all about vanity, you don’t want someone’s first thought upon meeting you to be, “Whoa, he looks nothing like his pictures.”

Not only is it insanely distracting, but it’s starting the potential relationship with dishonesty rather than trust. This also goes for exaggerating, or outright lying, when it comes to your job, education, or anything you find yourself tempted to say to get a meeting in person. I guarantee if they find out you tricked them, they will assume everything you’ve said was a lie.

And this isn’t to say that if you’re overweight, don’t bother. Dating sites have huge audiences, so you’ll find every stripe and color of person you could possibly imagine, and by misrepresenting yourself, you could be missing out on the people who like you for who you actually are. But on that note, not everyone on the other end will be honest with themselves, so…

2. Temper Your Own Expectations

While getting catfished, or tricked into falling for people who lie about everything (right down to using someone else’s pictures), seems to be the common assumption about meeting someone from the internet, it’s really not that common. It does happen though. This is why you should try to use the internet as a means of meeting people, and use subsequent in-­person dates to get to know them. You aren’t meeting someone with the intent of going ring shopping if things go well.

While dating sites have plenty of attractive and very successful people, not everyone will look exactly like their pictures. While I’m not saying you should be expecting a man in a wig to show up, you should kind of automatically assume that their pictures were old or edited, or at the least, something that shows their very best light. Not that that’s always the case, but just keep in mind that you can never truly know someone you haven’t talked to in the flesh.

3. Take the Lead in Conversation

Maybe you had an incredible conversation online with someone whom you decide to meet, and then they barely say a word. Meeting a stranger is always awkward, and online dating, especially, lends itself to folks who are shy in social situations. So you would probably be doing yourself a favor if you just lead the conversation (if you don’t know how, study this tutorial), or simply just deal with the awkward first date and see if either one of you would like a much less awkward second date; remember that it often takes 3 encounters to really know if you click with someone.

4. Accept Rejection

Does this seem like common sense? Because I have never been more embarrassed on a date than when I hear horror stories from the woman about other men she’s met online. And really, most of it comes about as a result of rejection. While the theory behind matching someone is that you are both mutually interested in each other, that does not mean you are halfway to dating. If a girl says “No” when you ask them on a date, take it in stride, and then move on.

Sadly, this isn’t what many men do. You can find an endless supply of screenshots online from women who were having a normal conversation with a guy, and when she says she’s not interested, he suddenly drops about every dirty word you can call a woman in the next message.

This tip also applies when someone flat out doesn’t respond. If you try to start a conversation and get nothing in return, don’t leave twenty more messages or take it personally. Maybe they don’t check it that often, deleted the app from their phone, or just aren’t interested. That’s life. Just be thankful it happened with a stranger from the internet rather than someone you approached at the bar.

The problem is that talking to people digitally really dehumanizes them. We lose track that it’s a person on the other end just like us, and we say things we would never say in person, bad or not, and so we throw out the common unwritten rules of socializing. This is also why it’s better to meet people as soon as both of you are comfortable, so you can put a human to the picture.

5. Stay on the Date, At Least for a Little While

When you finally do meet in person, it’s important to be as polite as possible, even if they look nothing like the image you had in your head. I’ve literally shown up on a date and only found out when I got there that the person was weeks away from giving birth. I didn’t leave or sneak off “to the bathroom,” but I stayed and had about an hour-long conversation, not because I’m a saint, but because I could not imagine someone telling me to meet them and then just never showing up. Most importantly, you can never be worse off for simply knowing someone. Even if the date is terrible, you are meeting someone who you probably would never have met, and your life is that much richer.

6. Try to Figure Out What They’re Looking For

This isn’t as cut and dry as it seems. While there are plenty of people who are indeed on Tinder and other platforms for the sake of finding relationships, they are also widely used for hook-ups and simply to further one’s own vanity. But generally, these people are easy to differentiate. If someone just wants sex they will probably suggest you either go to their place or they come to yours, so you can “Netflix and Chill,” which is just code for sex. A lot of people actually have “No hook-ups” in their bio, which gives you an idea that they’re looking for something a little more serious.

There are also a lot of people who are on these apps and sites just for attention. These people tend to match everyone just to feel better about themselves and try to get you to follow them on every social network they have a profile on. They will also never meet you, because they are simply on there for the ego boost and not to actually meet people.

Frankly, the best way to figure this out is to ask. Not right off the bat, but if you aren’t sure where things are going, you can ask in the midst of a conversation. If they respond that they want to meet new people and possibly find a relationship, that would be the perfect time to ask for a date.

Frankly, online dating can be a bit weird and awkward, especially for folks who didn’t grow up socializing on the internet. But if you’re single and looking to mix things up a little bit, give it a shot. After all, the worst that can happen is you have material with which to write articles about the do’s and dont’s of online dating.

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Jordan Zammit studies History at Michigan State University and bad dates at the University of Tinder. He has been using the Art of Manliness as his earthly “bible” since 2012 and is eagerly awaiting the day hats are no longer a hipster thing. You can follow him on Twitter @bae_z_.

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