In Bed With Gigi Engle: Should I Go on a Trip With a Long-Distance Guy I'm Into?

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.

Hi Gigi,

I've been reading your column forever! Thanks to you, I've started enjoying sex and being more open about it. Coming from a very conservative family, I was taught that sex is shameful and wrong. But your columns flipped that in my mind.

While traveling to Chicago back in June, I connected with "Z" on Bumble. We decided to meet at his place, kissed in the first hour, and I slept over. It all seemed casual and fine. I visited again in July, and the two of us had the most amazing, intimate weekend together.

Now, we talk on the phone all the time. One day, I sent Z a picture of my parents traveling in Iceland. His response was that he and I should go there ourselves. On a bit of a whim, we've now booked flights and are planning this trip together. The only problem is that now all I can think is that I shouldn't be seeing him again because he's in Chicago and I'm in California. I did fall for him. I don't know what to do. Please help!

-- C

Hey girl!

This sounds like a classic, ultimate battle of head vs. heart. I think we both know you're not going to let this go and just walk away. Would it be easier? Maybe. But this seems like a real connection. You have feelings for this guy and now you're stuck riding it out. We have all been there.

The heart does not listen to reason.

Z sounds like a nice guy. It does not sound to me like this dude is jerking you around. If I thought he was anything less than totally into you, I would tell you to cut and run like hell. This guy LIKES YOU! I have no doubt about that. It's great that you've gotten to know each other in spite of how difficult it can be to do this stuff long distance.

We can't control how romance takes us. I once met a boy in San Diego when I was 13 and I was positive I was going to marry him. I lived in Chicago at the time (how's that for coincidence?). We talked every single day for two years before I finally decided to move on with my life. Love gets under your skin and makes it impossible to shake.

C, life is too damn short to waste it on overthinking. You have found a man who wants to take off for frickin' ICELAND with you! It sounds like a grand adventure. I think you should GO, GO, GO! Have fun! Make passionate, sexy love in a field, in a hot spring, and on a waterfall.

I'm not going to BS you: Making a long-distance relationship work is extremely tough. But that doesn't mean you should skip out on this experience, and that doesn't mean there aren't tons of fun, creative ways to make this thing work. And no matter what happens, a random trip to Iceland with a cute boy you like is something you will never forget or regret.

I think this could be a true moment of maturity and growth for you. Don't be afraid to take chances.

Keep in mind that there aren't really any rules here. The two of you are already outside the norm with your unusual geographical pairing and whirlwind romance. But beyond that, there's nothing about your future together that's any more or less secure than anyone else's new relationship.

At this point, it's just about managing your expectations. Instead of worrying about the future, take the situation day by day.

Pay close attention to your feelings. If the sadness you feel being apart starts to outweigh the happiness of speaking and occasionally visiting each other, reassess. Do what makes YOU happy.

At the risk of sounding super cheesy, just go with the flow. See what happens, and keep an open mind. You never know what opportunities await. Don't ever be afraid to take chances.

Love your favorite internet auntie,
XOXO Gigi

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