In Bed With Gigi Engle

In Bed With Gigi Engle: If You Meet Online, When Do You Meet IRL?

in bed with gigi engle
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Welcome to In Bed with Gigi Engle, a weekly column in which sex and relationships writer Gigi Engle answers your most intimate questions. Nothing is off-limits! From threesomes to anal, unrequited love to cheating: We want to hear it all.

For questions on relationships, sex, or anything else, email Gigi at AskGigi@thrillist.com.

Dear Auntie G,

I met this guy online and we instantly hit it off. We live in different cities, but he was coming to mine in a few months so we planned to meet up.

I had second thoughts about meeting him; so when he came to town, I was waiting for him to convince me. But instead, he said it was OK if I couldn't. We ended up not seeing each other. I felt bad about that, and figured it would be the last time I'd hear from him.

But as soon as he got back home, he messaged me saying he was sad we hadn't been able to see each other. Since then, we've exchanged messages here and there. Nothing deep, but our conversations are always pleasant and enjoyable. 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'm going to be in his city soon and don't know if I should see him. Help!

Love,
Dazed & Confused

Dear Dazed & Confused,

Going from online to meeting someone in real life is nerve-racking -- even if online dating is the new normal. You meet someone on an app or website, talk about everything, and then when it comes time to meet you can't help asking yourself questions like, Is this guy a serial killer? What if he looks nothing like his pictures? What if he likes the online version of me better than the real-life version of me?

We've all been there. It's a lot easier to be cool, calm, and witty when you have time to actually think and write out your responses. Having to emulate that same level of hilariousness in real life is a challenge. It's enough for any of us to ditch the whole date entirely and throw that prospect in the bin.

It's a lot easier to be cool, calm, and witty when you have time to actually think and write out your responses.

The fact that he was coming from out of town made the stakes that much higher. It was your "one chance" to really make it happen. To be honest, I can't say I would have gone through with it either. It sounds like you're an over-thinker like me. It's easier to just NOT. Was that the right choice? Maybe you regret it in retrospect; but you shouldn't be going to meet a stranger anywhere unless you feel totally comfortable with it. I'd say you just weren't ready.

Let's get real. Where was this really going to go, anyway? You don't live in the same city. What actual potential does this relationship even have?

I think you have to be realistic here. That outcome is highly unlikely. I'm not saying people don't fall in love over the waves of cyberspace and live happily ever after. It can happen. But given your letter, a passionate Notebook-style romance is not homeboy's intention. He didn't even put in the effort to see you when he was in town.

You asked if he's chatting you up because he's bored, and I would say that's exactly what's happening. He knows you're available and lonely, so when he's available and lonely, he can hit you up. He's not actually serious about you, girl -- you even openly admit your conversations don't have a lot of depth to them.

Let's get real. Where was this really going to go, anyway?

Sounds to me like you're projecting a fantasy on this guy because YOU are bored and want love. There's nothing wrong with that. He's far away and it's easy to make someone you've never met into the man of your dreams.

The problem is that he's going to disappoint you. He hasn't even shown a lot of interest in you; or at least, not enough to get excited about. If you do decide to meet in person, get yourself some realistic expectations.

There are two possible outcomes in this situation: 1) He is going to be a big let-down, end up being flaky and unreliable, or just not as fun as you thought. That will make you mad and kind of heartbroken because you'll feel like you wasted your time. 2) He'll wind up being great and it won't be able to turn into anything because YOU DON'T LIVE IN THE SAME PLACE.

Don't wrap yourself up in this fantasy or you'll wind up missing the REAL thing.

If I were you, I'd just accept this for what it is: a loneliness bandage for both of you. Don't wrap yourself up in this fantasy or you'll wind up missing the REAL thing when a guy who actually lives in your hometown wants to be your boyfriend. If you can't let go of the fantasy, don't talk to this guy anymore. He sounds pretty basic, anyway.

Love your favorite internet auntie,
XOXO Gigi

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For questions on relationships, sex, or anything else, email Auntie Gigi at AskGigi@thrillist.com. Follow her on Twitter, iTunesFacebook, and Instagram. For more In Bed with Gigi Engle, click here.