Skip to main Content

I’m in my late 30s, newly single and ready to mingle — but how?

  • Author: Wayne and Wanda
  • Updated: October 13, 2018
  • Published October 13, 2018

Dear Wayne and Wanda,

I was in a long-term relationship for many years that had turned into something pretty platonic and romantically unfulfilling. The breakup was a long time coming; we finally ended things a few months ago, and now I feel ready to date.

You might think I'm moving too fast, but keep in mind this relationship was basically over months or years before we pulled the plug, so I've had a long time to get used to the idea of moving on. The problem is I just don't know how to go about it. Here I am, single and in my late 30s, and I can't remember how to even go about dating.

So far my first attempt was a fail. There's this guy I've been crushing on, we work together, and the other night, I suggested we hang out. At first he was all over it — I don't think he realized I meant as more than friends? So when we met up for drinks after our shift, I tried to flirt — I'm sure I was an awkward disaster, but I think my point got across because at the end of the night, he started talking about how special I am, and how he's always thought so, and I'm "too good" for him, and he couldn't imagine dating right now because he's so busy.

But then at the end of the night, when I asked him in, he came in, and we made out, and it was awesome! Then he left abruptly, and I felt completely confused. First he seemed to be gently letting me down, but then he was all over me, and then he was gone! Talk about mixed messages.

I think I could have something with this guy, so part of me wants to keep pushing it, but then again, should I forget him and "put myself out there," and how exactly does one do that? I feel like I'm going about this all wrong. Help?

Wanda says:

I hate to be the bearer of bad news, but you actually didn't do anything wrong in the above-described scenario; you simply experienced the same mixed messages, bad communication, nerves, angst, hope, and physically-driven impulses that fuel oh-so-many dates every night of the week in our beloved town. Look: Dating is hard. Not dating after so many years will be even harder. Summon every ounce of patience at your disposal as you wade back into this murky and turbulent pool.

Is this guy into you? Maybe. He kissed you! But, maybe not. His rhetoric at the restaurant sounded awfully "he's just not that into you." Only time — and patience! — will tell. In the meantime, cheers to you for putting yourself out there and so boldly issuing an invitation. This speaks to your confidence, which will be your biggest internal support as you re-enter the mysterious kingdom of the single and available.

Here's something else to keep in mind, especially if you're looking to your existing circle for romantic partners: While you've been ready to move on for some time, they might not know that, or believe that. In fact, they might assume you're still processing the past, or in rambunctious rebound mode. Frankly, both are unattractive options for a potential partner, who fears a night with you might entail you complaining about your past relationship, or alternatively, ruthlessly using them as a sexual springboard to the future. Clear communication about where you're at mentally and emotionally will help you negotiate these landmines.

Wayne says: 

Hey, if you're confident you're ready to dive back into the dating pool — and you certainly sold me — go for it. But, like Wanda said, just because you're single and ready to mingle, don't expect everyone else to be on the same page or running at the same pace.

Take, for instance, your co-worker crush. Step back and look at this from his perspective. You guys have worked together for a while, if not forever, and suddenly you want to hang out after work. Hmmm, that's a new development completely out of nowhere, but OK. Then, just as suddenly, hanging out turns to making out. And then making out turns into getting the heck out.

Eight hours earlier you were talking about the new cover sheets for the company TPS reports. Now you're going all NSFW on him. Hello, blindsided! How do you do, confused?

Maybe he is into you, maybe he isn't. You might want to try a real date or five with him to figure that out instead of weighing it all on a night out of drinking and buzz-fueled smooching.

Local news matters.

Support independent, local journalism in Alaska.