Dear Wayne and Wanda,

I’m kinda stuck in a tight spot with my girl. She’s got this summer all mapped out with like five trips out of Alaska, and she’s dead set on dragging me along for the ride. We’re talking three weddings, a big family gathering with all her siblings and their significant others — which apparently is a once-in-a-blue-moon deal — and the annual music fest with her college crew and high school buddies. I get why she’s feeling the pressure to show her face everywhere, and sure, why she wants me there. But man, it’s a logistical nightmare and a wallet-drainer, not to mention all the vacation days I’d have to burn. Plus, I’m not exactly thrilled about ditching our Alaska summer vibe while she jets off.

We’re both pushing 30 and have been going strong for almost two years now. Come fall, we’re planning to shack up together. We’re pretty much on the same page about everything: future, family, the whole shebang. Alaska’s been home for us since we each moved up after college and eventually met, and we’re both very happy here.

This whole summer ordeal is our first real “drama,” and it’s not just me feeling the heat. I know she’s stressed and feels pressure, but she also keeps talking about needing to RSVP, buy tickets and make reservations. I get it, but I feel cornered. I’ve suggested we prioritize these trips, pick a few for her and both of us to attend, and figure it out together, but she’s adamant that they’re all crucial, while at the same time putting pressure on me to make the choices. It feels like a trap.

I want to be supportive, and present, but I’m frustrated. How can I support her while keeping some boundaries and making her see my reality?

Wanda says:

It’s admirable that you’re trying to be a responsive partner, so let me state the obvious: Missing one or more of these trips does not make you a bad boyfriend. On the low-end estimation, five trips would have you out of Alaska for at least 15 days, and that’s if you were leaving on Fridays and returning on Sundays, or something similar. More realistically you’re looking at being away for several weeks cumulatively. That’s practically one-third of the summer. And if it’s anything like the past couple of summers and all the miserable rain we’ve had, you could end up missing all the best days.

I’m not telling you anything you and your girlfriend don’t know: Alaska summers are awesome. It’s the absolute worst time to leave. It’s why we suffer the winters — to play in the late-night sunshine. Five trips is just too big of an ask. I’m sure even she knows this and is hoping your devotion to her will win out. But this is a perfect example of where a compromise is in order, and where both partners of the relationship should agree on and respect that compromise.

In your case, let’s consider the list. Three weddings? That’s two too many. Pick the one where you have the closest connection to the bride and groom. Not close to any of them? Then default to whoever is nearest and dearest to your girlfriend. The family reunion? Skip it. If it’s truly a rarity, everyone will have their hands full trying to create meaningful reconnection amid the crowded chaos; your presence, quite simply, isn’t a value add. Make sure your gal has a recent couple selfie snapped on her phone that she can show off to all her aunties. Finally, the music festival? Go! This is the only thing on the list that sounds like a real vacation. Propose this plan to your partner, explain the thought process, and promise when the tables are turned in the future, you’ll remember to be lenient in requesting her participation.

Wayne says:

Following last week’s dramatic NFL Draft, I feel compelled to grade your selections, Wanda. While you made some solid picks, and wisely advised him that backing away from a few opportunities would fortify his front office synergy (mental health and relationship stability) and salary cap (financial health), I must grade your collective selections a C because you totally botched the most important pick: the family gathering.

If our letter-writer sees a future with this woman, it also means a future with her family. And if he’s the only partner not attending this rare get-together, it sends a pretty loud and not-so-cool message (or messages). The family will talk, to her and behind her back. And she’ll have to answer for him, which is exhausting and embarrassing. “He’s hiking” or “He’s hanging out in the backyard drinking beers with his buddies under the Midnight Sun” won’t exactly score a free pass or points with the family.

But yes, you must compromise and sacrifice. And yes, you must be the good boyfriend. So, I suggest you attend three events, in this order: 1. The Family Gathering (reasons listed above); 2. The Most Important Wedding to your Girlfriend (obvious reasons); and 3. The Friends Festival — the biggest bang for your buck in solidifying yourself with the people she cares about (and if you’re going to miss summer sun in Alaska, summer sun and fun at a humid outdoor festival is a great trade).

And yes, remember that she’s stressed and feeling pressure, too. When you tell your girlfriend about your Top 3 choices, also work to remind her that life is long and you two have big plans, too. And that it isn’t the end of the world if she attends one wedding with friends and skips one wedding to give herself a reset of basking in Alaska’s summer, and get some quality time with you while plotting your big move. If she has a sense of humor, tell her that statistically one of the marriages will likely end in divorce anyway. Send the losing pick a nice gift and invite them up to Alaska to stay with you on either end of their honeymoon. Now you’re going from a no-win to a win-win. Have fun!

[Ask Amy: My girlfriend got drunk at a party and revealed deeply personal info about me. What should I do?]

[Ask Amy: My boyfriend’s a great guy and we were talking about marriage. Then I discovered he’s nearly $20,000 in debt.]

[Wayne and Wanda: Why do I feel jealous of my boyfriend’s close friendship with another woman?]