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Should I ask my summer fling to ditch his seasonal lifestyle and stay in Alaska?

  • Author: Wayne and Wanda
  • Updated: August 17, 2019
  • Published August 17, 2019

Dear Wayne and Wanda,

I met the guy I’m seeing back in May when he came to Alaska for a summer job. Even though I knew he would eventually be leaving, I got involved and fell for him pretty hard. We have had the most amazing summer so far and I really think I’m in love. We haven’t officially said we are a couple, or exclusive, but I think that’s because we both have always known he was leaving.

He’s said from the start we needed to keep this simple and casual since he plans to leave sometime in September. But we have spent almost every night together, gone on killer camping trips, had some really romantic times. Lately he’s been talking about things after September — like me meeting up with him this winter in Mexico, or getting together around spring break.

This has me thinking he must have developed feelings too. We still have at least a month until he goes and I feel like now is the time to put my cards on the table and tell him how I feel — and ask if there’s any chance he would stay. Some of my friends say to go for it and some say it will freak him out. I don’t know what to do, but I know I don’t want to lose him.

Wanda says:

It’s hard to lose what you don’t have, I’m sorry to say. As much as your feelings may say otherwise, your behavior and the casual terms you’ve agreed to for months now have established a very different reality.

In reading your letter, I’m picking up on a lot of assumptions on your part. For example, you assume his reluctance to embrace a title and monogamy is due to his impending departure. You assume his inquiries about future meet-ups are due to intense feelings on his part.

But here’s another way to read it: Maybe he’s a free-spirited globetrotter who follows seasonal work with rarely a backward glance and he totally hit the jackpot by landing a summer with you, a fun-loving and affectionate gal who was happy to meet his no-strings-attached terms.

This arrangement between the two of you seems to be full of fun and frivolity, but what it’s missing — besides a mutual formal acknowledgment that it is actually a relationship — is communication. So rather than dive-bomb the poor guy with an invitation to move in and stay forever, start small. Talk about his next steps. Ask if he’s considered putting down roots. Share that you’ve become truly attached. And see what happens next.

Wayne says:

Wanda’s right — you certainly don’t have to show all of your cards yet. There’s still some summer fun to be had, after all. But unless you want to drive yourself crazy, you should play at least one card now, maybe like the second-best card in your hand. Probably a little something like, “Sure, I’ll meet you in Mexico, if you come back to Alaska to ski with me during spring break …” (wink wink).

That should get the conversations moving on a light note while also giving you some immediate insight on his feelings, as well as his short-term and long-term intentions. Depending on how he responds, then you can consider throwing all of your cards down or playing the ace up your sleeve: You like him a lot, you don’t want him to leave. Now that’s a riverboat gambler pushing all in right there.

If that scares him and he runs, well, he was going to leave anyway. If it makes the rest of the summer awkward, oh well — it was probably going to get awkward eventually. If that brings you two closer and suddenly there’s a future beyond this summer, jackpot!

Either way, summer flings and the subsequent bittersweet falls are practically a tradition of romantic coming of age. It’s easy to get lost in the sizzle, swimming and sunburn as the summer races by. But then the sun starts to set on summer and the relationship, and a cold, dark autumn awaits. I know it’s difficult to envision now, but at the very least in a few years, every time spring wraps up and summer rolls around, you’ll have a nice memory to smile back on.