That Girl: Dating In Your Thirties (Ep.1)


Imagine this: He has killer hair, a perfect smile, the style you dig most, and those undeniably sexy vibes. And, the cherry on top, he blushes when he meets you. You know he’s young, but who cares? You’re into it from the start.

Then, and this is inevitable, he talks. About weed. About his favorite cocktail concoctions (from a bar cart he wheels around his neighborhood for people — you can’t make this sh!t up). About the oddly-elaborate hiking adventures he takes with his “bros.” About how proud he is of the 5 speeding tickets he’s gotten in the past 24 months. And you’re slapped with the harsh realization that age is not “nothing but a number.” 


This gets better, right?


I’m 32. Single. And dating. And I think I hate it.

My story sounds like another Bridget Jones cliche: I never thought I’d be here. I’ve had two serious relationships, and been pretty close to the “Till death do us part” thing twice. Close… but no cigar.

If you would have told me in my younger years that I would still be single at 32, I might have punched you. Or cried. Or both. Life, man. It’s a doozy.

But alas, here I am. And I intend to make the best of it. Perhaps you want to come along for the ride?

After intense singledom (saying no to any and all date requests) for nearly two years, I decided that now is the time. It was not some huge, momentous thing – me deciding I was ready. I mean, are we ever really ready? But a month ago, I jumped in. And now that I am saying yes instead to these requests, and even requesting some of my own, I am finding out, well… this kind of sucks. People are weird. And am I really relying on a matchmaking app to pick a soulmate? Discovering that deep conversation is, I don’t know, not a thing that happens anymore? And, did I mention… people are weird?

How it’s supposed to feel

To be fair, small talk is not my favorite pastime. And do you know much of it you have to do when dating? Let’s just say it’s a lot.

“What do you do for a living?”

“Where do you live?”

“Where did you grow up?”

“What do you do in your spare time?”

Blah, blah, blah… And what’s worse? Doing this shit on an app, from my phone. I feel like my fingers can manually type my answers for me at this point, and it’s only month #2. I really should just write it all out and screenshot the shit for my next conversation.

Same questions, same answers. Every time.

But, what is the alternative? You can’t really skip the get-to-know-you basics. You can’t jump in to, say, how to raise a child or where you want to grow old or big life goals in the first couple breaths. I mean, you could, but you’d probably get ghosted.

How it really feels

There are, of course, a few that keep things interesting. I had a guy tell me all these lovely things he’s looking for in a partner. Super romantic-like. Proud. Just as I was about to propose we skip happy hour and go straight to the little white chapel, I hit the last stanza where he says he would want, no need, his woman to “really be a woman” (implying I may not actually be a woman) because, well, he said, “…some people may be into that but I’m not.”

Okay? Is this a thing? Is this man constantly falling in love with women only to find out later that she was actually born a he? Or is he just that transphobic that he feels the need to preface any possible second date with this disclaimer?

Either way, it was a hard pass from me.

The next one will be better. I know it. I’ll tell you all about it next week.

Think of this as something of an advice column in reverse. Are you single people experiencing these things, too? Give me advice. And all you non-single folks, perhaps you want to tag along for a few laughs while getting a heavy dose of appreciating-your-significant-other. Are you into it? I am if you are.

Allison, “That Girl with All The Dates,” is a 32-year-old Client Relations Manager at a tech firm in Minneapolis. While her job, her books, her beloved cat, and her nights spent dining at the Twin Cities’ greatest restaurants certainly provide a fulfilling life, she still hopes this whole dating thing will work out one day. Get in touch:

And, for more thoughts on dating and the way people meet people in the modern age, read this next: Tinder: Good or bad for Twin Cities’ singles?