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He’s older and recently divorced; I told him I want fun, but he wants more

  • Author: Wayne and Wanda
  • Updated: February 1, 2019
  • Published January 30, 2019

Dear Wayne and Wanda,

I am a single woman in my mid-20s who moved to Alaska a couple years ago and has very much enjoyed settling into my new job and getting to know this beautiful place. I didn’t know anyone when I got here, and I turned to online dating pretty early on as a way to meet people. Recently, through Tinder, I matched with “Jack.” He’s in his early 40s, which is at the high end of my allowable dating range, but he doesn’t look his age at all. He’s super cute, has a good job, seemed fun from his pics, so we started talking. I learned he recently divorced, and he said he was just looking to relax and have a good time.

When we met, it was totally epic. We started with a super nice dinner, which turned to drinks, which turned to Jack suggesting we drive to his Girdwood condo for the night. Um, yes! We then had the most amazing night together, and because the weekend was just beginning, decided to stay down there another night.

Since then, Jack has been texting me nonstop and I’m not sure how to handle it. We both agreed up front we didn’t want anything serious but that’s not how he’s acting at all. He is getting way serious with his words – instead of simple flirting and casual talk, he’s telling me how amazing and incredible I am and how he can’t stand to be away from me, etc. I want to be clear: in no way do I feel threatened. I just feel annoyed. I told Jack I just wanted to have some no-strings-attached fun, and the guy has gotten super attached! Are all older men like this? And is there a way to get him to dial it down a little or do I need to just cut him loose?

Wanda says:

Oh girl, you don’t know Jack, and by Jack, I mean Jack and all the men out there just like him: just-divorced, desperately lonesome, completely unaccustomed to sailing solo, and while some primal male urge long buried within prompts sentiments like, “I’m not looking for anything serious,” in reality, Jack is adrift and desperately seeking his next monogamous mate.

Seriously, I’ve seen this play out so many times. Guys get out of long marriages, and then – they get married again! Like, super fast! Or at the very least, they dive into some really serious commitment. I can’t put it all on the men here. Women do it too. Maybe it’s biological, maybe its socialized instincts, maybe it’s just something that worsens with age, but it’s a real phenomenon: people who’ve been tied down for a long time get cut loose and then begin looking feverishly for a new anchor.

Can Jack be changed? Perhaps. But you need to be clear with him (apparently more than you have been) about what you want (which sounds like, just sex? And condo weekends?). And you need to be ready to cut and run if Jack isn’t hearing you. He may not be in a physical or emotional space where he can understand your mindset.

And no: not all older men are like this. There are plenty of happily confirmed bachelors (and bachelorettes) who play the field and keep things light by choice. There are also a fair share of divorcees who enjoy a reprieve from relationships. So don’t be turned off eternally at the prospect of May-December romances.

Wayne says:

This isn’t an age thing; this is a state of mind, bad timing; and false advertising thing. Or things. And while your state of mind is fun weekend flings in Girdwood or wherever, Jack’s state of mind is fun weekend flings in Girdwood followed by five weekdays of hanging out every night, texting and talking every day, connecting and communicating whenever possible, and increasingly depending and relying on someone else’s presence.

Too bad about Jack, but some people are lost and really don’t know what they want. You clearly do, and if you’re honest about that with Jack, as well as honest about how he’s acting as opposed to what he’s saying, maybe he’ll have a moment of clarity and delete his Tinder app and get on eHarmony …

Either way, move on. He isn’t going to not want to spend more time, and get serious as quickly as possible, with an exciting young woman while the ink is still drying on his divorce papers. If he doesn’t get it or back off, ghost and block him. He might be mature in age, but he clearly hasn’t learned how to play well with others.

Don’t give up, though. There are a lot of Jacks out there, but there are also some gems of all ages in the dating pool who are just like you – happy with their current situation, honest with themselves and others, and looking for good times around Alaska. They don’t all have Girdwood cabins, of course, but I have a sense you can have fun in most settings. Enjoy it.