Should You Meet A Guy From A Dating App IRL? As Told By A Nice Guy And A F*ckboy

by Adam Shadows
Kylah Benes-Trapp

Dear Nice Guy and Fuckboy,

I met this guy online who's miles away from me. We instantly hit it off and continued talking because he would be in my city in a few months.

I'm not the flirty type, so whenever he tried to flirt with me, I usually shrugged it off. (By the way, we had FaceTimed, so he is real.) Maybe because I always shrugged off his sweetness, our conversations diverted to platonic topics, like his travel plans.

I'm not really comfortable meeting guys online, so I had second thoughts about meeting him when he was in my city. I was waiting for him to convince me to meet him, but he acted cool about it, like, "It's okay if you can't."

We don't have deep conversations, but I feel he likes talking to me.

So, I ended up not seeing him. I felt really bad about it and I thought it would be the last time I'd here from him because what's the point?

But as soon as he was back home, he messaged me saying he was so bummed we didn't see each other and he misses my city. Now, we don't talk regularly, but I still get messages from him once in a while telling me, again, how he misses my city or asking how my city is doing.

We don't have deep conversations, but I feel he likes talking to me.

Is he just bored? I feel like I like him, but maybe he talks to me only when he's bored. I can't figure him out. Should I continue talking to him? I'll be traveling to his city soon, and I don't know if I should see him. Help!!!

Love, Dazed&ConfusedinCharlotte

Kylah Benes-Trapp

Hi Dazed&ConfusedinCharlotte,

I'm a little confused myself. You haven't even met this guy yet, so whatever judgements you're making at this point are far too premature. He's flirting with you, and you are (as you stated) shrugging it off. If I were him — scratch that — if anybody were him, we'd think you weren't interested in us at all.

Dazed, I hate to say it, but you've manufactured a non-issue into a situation you haven't even given a shot.

The fact that he's still talking to you is evidence that you've left an impression on him. So no, he's not bored. Trust me, a dude who was just bored would have given up by now. At this point, you've given him no reason to stay.

You've manufactured a non-issue into a situation you haven't even given a shot.

I feel like there's a good chance he might have this same “Is she just bored?” concern about you. I mean, he came to your city, asked you to meet up and you didn't because he said it's "OK" if you couldn't?

I'm sorry, but what?

I've said the whole "It's OK if you can't" line to almost every woman I've dated. He didn't say this to be cool — he said it because he was nervous and being considerate.

He didn't expect you to meet him, so instead of being super confident and giving you a definite date and time (which he should've done, but not all of us are Casanovas), he gave you an easy out, which you took... again.

Want to know if a guy likes you? He initiates conversation.

And yet, here he is, still desperately trying to keep communication alive, despite you not putting in any effort.

His latest question, "How is your city doing?" means he wants to talk to you, but doesn't have anything to talk about because he still doesn't know much about you.

Want to know if a guy likes you? He initiates conversation. This guy digs you, Dazed!

But, in a way, you're villainizing him. Why, I'm not sure. Could it be the distance? Have you been hurt recently? Are you sure you're ready to date?

To be totally honest, I think the only reason these interactions have become stagnant is because of your own apprehension. He's made his feelings as clear as he possibly can without coming right out and saying them, yet you're not even meeting him halfway.

That's my advice to you: Meet him halfway, metaphorically and literally. Go out and actually meet this guy. Choose a date, a location in between your two cities (or when you're in his) and actually go this time.

Meet him halfway, metaphorically and literally.

That way, you've both put in equal effort and you can start this date on an even playing ground. It could have the same romantic result like when Miranda and Steve reunited on the Brooklyn Bridge, or it could be a travesty, like when Summer left Seth for Zach.

You've got nothing to lose. You yourself say he's sweet, so find out if there's chemistry. See him when you're in his town.

Stop bumming this guy out, Dazed. He's worth a shot.

Best of luck!


Kylah Benes-Trapp

Dear Dazed&ConfusedinCharlotte,

Alright, alright, alright.

Now, I hesitate to respond to your question with my usual, all-or-nothing vitriol. Usually, I'd say screw it. It doesn't matter if you haven't talked in a while. Take that leap. Take the chance. It's one night. Maybe it'll be great, and you don't want to regret not trying. What do you have to lose?

But I can't do that right now, not when it comes to this. As a man, I'll admit I cannot completely comprehend the reality of your situation or attempt to crunch the calculus involved in deciding whether or not meeting a relative stranger is a good move.

It's because of the fact that you women face dangers in this world that men don't.

You women face dangers in this world that men don't.

And while I think the still-widespread — and often comically communal — apprehension for and stigma towards online dating remains horribly overblown, I'm not ignorant enough to consider women susceptible to absolutely zero risk with these types of things. The Craigslist Killer was real, at least.

While it's more than severely likely this dude has nothing but his dick's best intentions at heart, I simply wouldn't be able to go on if my advice steered you toward some kind of peril in any way.

My hands are tied. I can't tell you, Dazed, what to do or what not to do. All I can do is share an experience of my own and hope it resonates. I know that's not what you came here for, but maybe you'll leave satisfied all the same. (In a way, you're not unlike most of the women I bring home.)

Here's what happened to me recently:

I've met several women online since I began writing on this website, whether it was on Twitter, in email, in the comments section or something else. Before I knew it, we were texting.

All I really knew about these women is what one picture and the ten digits of their phone number showed. In a weird way, these online relationships have a tendency to become some of the most intimate of all. It's a phenomenon only our generation understands.

All I really knew about these women is what one picture and the ten digits of their phone number showed.

Anyway, a few of these women worked their way under my skin. One, in particular, did me pretty dirty. We were talking every day, for hours and hours on end. This was, in so many ways, a better form of courtship than an in-person first date or a blind date.

We were able to discuss important topics — things that mattered to us that might be harder to articulate out loud — like philosophy and politics and the pleasures of pussy-rubbing. We were also sexting constantly.

We had trust and an abandonment of all bullshit, and all these things came loaded in a deadly, powder-keg combination of incredible intrigue and a complete lack of consequences.

We started to like each other. But that didn't change the fact that she lived hundreds of miles away.

We started to like each other. But that didn't change the fact that she lived hundreds of miles away.

She planned to come to the city in a month or so, so we looked forward to that. I had reason to think we'd spend some time together and it would be great. Neither of us could wait for the real thing; it almost became painful.

Then, finally, she came here for a few days... and immediately vanished.

For the first time in months, it took her hours to reply. Then — beep — she was back, briefly. There were excuses: Her friend was doing this, she lost her wallet with her ID in it or something was happening at a gallery on the West Side and I wasn't invited. All this bullshit.

The first day came and went.

The second day, there was a rock show she had tickets for, and we had plans to meet before it at a bar. I went to the location, and — beep — she said she would be an hour late. Her friend was stuck at work. Then, she'd be another hour late. She couldn't take the train alone.

Then, the show started and she said we could meet after. I tried to understand. I waited, I drank beer and I killed time talking to idiots.

I kept waiting for her because I felt our time connecting warranted some responsibility.

I kept waiting for her because I felt our time connecting warranted some responsibility, that it almost birthed a duty in me. I didn't know if this duty was to her, to myself, to us or to this ridiculous time we live in, where you can feel obligated to someone you've never met as if that's completely normal.

I began to think about how nobody from any other time in history would be able to understand this particular plight. Then, I ordered another beer, drank it and left.

The second day came and went.

The third day, she apologized. I asked how the show was. It was great (what a surprise), and she sent me videos. She finally had her wallet. Eventually, we decided we'd meet at the bar that night, her last night in town.

I texted her a few times and didn't hear from her until after midnight. I kept drinking and waited. By that time, it was 2 am, so I called her.

She was back at her apartment already, giggling at the whole thing.

I called her a fucking tease. She cursed and screamed, and after I hung up, she texted me saying how weak I was — how she thought I was a real man. I deleted her number.

My point is, these types of relationships can be tantalizing, but dangerous.

My point is, these types of long-distance texting or online messaging relationships can be tantalizing, but dangerous. They're thrilling, they're immediate and they're always surprising you.

But the problem is, they often foster only an illusion of intimacy. And intimacy stripped of any actual allegiance to the person isn't intimacy at all.

When you mistake this for something real like I did, you end up even more dazed and confused than when you began.

Unfaithfully yours,