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Will pursuing this summer fling leave her with fond memories, a broken heart - or both?

  • Author: Wayne and Wanda
  • Updated: July 13, 2019
  • Published July 13, 2019

Dear Wayne and Wanda,

Back in early June, I met “Jeff.” He was literally just off the plane, having flown up to work as a chef at a lodge on the Kenai Peninsula. He offered to buy me a drink, and we ended up spending the entire evening talking, and he kissed me goodnight. We spent the next five straight days together. I spent any time I wasn’t at work with him, he stayed the night at my place, and we had the most amazing time getting to know each other, and crazy chemistry. Yes, I knew he was leaving for his job, but things were going so well, I figured we would figure that out when we needed to.

Once Jeff was gone, he went on to spend two days in Girdwood (I went back to work), then went on to his lodge, and it was just radio silence. I texted a few times and heard nothing back. Finally days later, he called. He told me all about the lodge, his job, the guests, but said nothing about us, or about maybe seeing each other again. So later, I texted to suggest maybe I visit him down there. His response was that he’s only here for the summer and doesn’t want to be in a relationship, or have anything serious, and that after Alaska he’s heading to Europe.

Well, I was crushed. I felt like we really connected. Then to add insult to injury, I saw on his Facebook some pics he was tagged in — some selfies with some cute hippie girl in Girdwood. Ugh.

But after all this, Jeff texted again yesterday to say he was thinking about me and it would be cool if I visited.

I am tempted to go. My girlfriends are saying not to waste my time, but it’s been so long since I met anyone interesting and we had so much fun together. They say he’s just using me, but isn’t it possible after some time apart, he really misses me? Should I go or not? I don’t know what to do.

Wanda says:

Go — if you just want a hot hook-up in a rustic locale with someone you’ll probably never see again. Go — if you can truly emotionally disconnect and appreciate the freeing physicality of a just-sex situation. Go — if you can reconcile the fact that this guy was done with you the second he was south of the Rabbit Creek exit and took less than 48 hours to find another Alaska conquest.

Or how about, don’t go. You don’t sound like a woman who’s looking for a fling. You sound like you’re searching for something more meaningful. To be clear, there is nothing wrong with flings, with flinging with wild abandon, with having meaningless interludes with hot chefs — if that’s what a person wants.

But be honest with yourself: You aren’t considering this simply because you want some physical companionship; you’re considering it because you’re holding out hope that Jeff really likes you, when all signs point to the fact that he’s just not that into you. Those signs include Jeff himself very straightly telling you that he’s not in this for any long haul, or even short-term haul. (Note to all the Jeffs out there: Honesty is great, but it would have been nice had Jeff mentioned that sooner, before commandeering our gal’s time, and heart, and bed, for five straight days.)

Wayne says:

So what’s your definition of a waste of time? Going to an amazing remote Alaska lodge for a few days of action-packed adventures in the wild and in bed (or in the tent) with a really cool dude sounds like a pretty darn good time to me. And, really, what else do you have going on right now? Not going sounds like a waste of time to me.

Will you leave with moments that you’ll remember forever? No doubt. Will you leave feeling bittersweet? Sure. Brokenhearted? Only if you allow yourself to.

And let’s keep everything in perspective here: You spent less than a week getting to know a gypsy who travels the world working tough jobs in cool places, making just enough money to get him to the next tough job in the next cool place. Meeting amazing people along the way is one of the bonuses of the journey. Don’t expect him to drop anchor right now, anytime soon, or maybe ever. And don’t take it personally that he isn’t stopping his traveling or his meeting new friends ways for you. Feel thrilled about the opportunity to spend time and have fun with him. And make sure your passport is updated because you can follow this guy around the world until he either realizes he wants to chase you back to Alaska or until something more exciting comes up in your life. Win-win.