Ask Anna: Am I into him or just into the uncertainty?
TNS/Freelance Stories

Ask Anna: Am I into him or just into the uncertainty?

Anna Pulley, Tribune News Service | August 5, 2026

Dear Anna, I’m 44, divorced, and very happily in my “slut era.” I’m dating casually, having fun, and not looking for either one-night stands or The Love of My Life. I’m somewhere in the middle. I want chemistry, good conversation and sex with people I genuinely enjoy spending time with, even if it’s not headed toward forever. A few weeks ago I met a guy on the apps who’s thrown me for a loop. ...

Casual dating doesn’ t mean lowering your standards for how you want to feel, writes Anna Pulley.

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Dear Anna,

I’m 44, divorced, and very happily in my “slut era.” I’m dating casually, having fun, and not looking for either one-night stands or The Love of My Life. I’m somewhere in the middle. I want chemistry, good conversation and sex with people I genuinely enjoy spending time with, even if it’s not headed toward forever.

A few weeks ago I met a guy on the apps who’s thrown me for a loop. He’s ridiculously handsome and has that mysterious, hard-to-read energy that somehow makes him even more attractive. The strange part is that over text he’s funny, thoughtful, sweet, asks about my week, remembers little details and seems genuinely interested in me.

Then we meet in person and it’s like someone swapped him out. The first time there was a lot of stilted small talk, he barely asked any questions about me, etc., but I chalked it up to shyness or first date jitters. The second time was genuinely great: He opened up a little, we talked for hours, the sex was fantastic. Then the third time was back to the first-time version — stilted, distant and he was out the door so quickly my head spun.

We’ve slept together three times, and after the last time I walked away thinking, “Well, that’s over.” I was so convinced he’d ghost me that I started mentally composing the story I’d tell my friends about it.

Then two days later he texted like nothing had happened. The banter picked right back up, and to my annoyance, I found myself excited to hear from him. Now I’m wondering if I’m attracted to him or to the confusion. Is this just a mismatch between texting chemistry and in-person chemistry? Am I inventing a mystery because he’s emotionally hard to read? Is the good night proof there’s something real here worth sticking around for? Or am I being delusional? — Confused Over My Era of Sluttery

Dear COMES,

(LOL.)

It sure sounds like you’re spending a lot of energy trying to solve this dude. Is he shy? Guarded? Socially anxious? Why is he more expressive over text? Is he avoidantly attached? Secretly into you? Secretly not into you?

The truth is: I don’t know — and you probably won’t either. But here’s the thing, you don’t actually have to know. The more useful question is simpler: How do you feel after spending time with him? Not while you’re waiting for his text. Not when the banter is flowing. After you’ve actually been together.

And I want to be careful here, because your letter isn’t describing a totally consistent bad feeling — it’s describing two off nights bookending one genuinely great one. That’s curious. It means you’re not just chasing a fantasy that only exists over text. You’ve had real, in-person proof that connection with him is possible. Which makes this harder because now you’re not just deciphering a mismatch between texting and in-person — you’re trying to figure out why the in-person version of him is so inconsistent.

You’ve had two encounters that left you deflated, one that left you closer. That’s not exactly a pattern yet — it’s one data point in either direction, plus a tiebreaker. Though it’s worth noting that the last time was so off that you expected to be ghosted, which is not something to ignore.

One thing I notice is that you describe what you want remarkably clearly. You’re not looking for forever. You’re also not looking for anonymous hookups. You want chemistry, conversation and enjoyable sex with someone whose company you genuinely like. Nothing in that description requires exclusivity. But it does require enjoying the actual time you spend together.

It’s tempting to give disproportionate weight to the texting because it’s warm, playful and leaves you wanting more. But text messages are not the relationship. They’re the trailer. The movie is what happens when you’re in the same room.

And to your point, there’s another possibility worth considering. Uncertainty is exciting — not necessarily because we’re broken or traumatized or secretly addicted to unavailable people, but because uncertainty itself is stimulating. Our brains are prediction machines. When someone is inconsistent, we naturally spend more time trying to figure them out than we would someone who’s straightforward. Isn’t that annoying? Thanks, brains!

The more time you spend trying to solve someone, the more significant they begin to feel. Not because they necessarily are, but because you’ve invested so much attention and time on the puzzle. And a good night doesn’t cancel that out — if anything, one great night in the middle of two off ones is exactly the kind of intermittent reinforcement that makes a puzzle more addictive, though not more solvable.

Here’s where I’d actually say something to him, rather than just gathering more silent data. Next time you’re together, pay attention to whether he seems present, whether he initiates rather than just responds, whether the good version of him shows up when there’s no obvious reason for it.

But don’t stop at watching. Say something! Like: “I’ve noticed our in-person time feels really different depending on the day — sometimes we click, sometimes it feels like you want to be somewhere else. What’s going on for you?”

This isn’t a relationship audit or a confrontation. But do ask him. His answer won’t tell you everything, but it’ll tell you far more than several more weeks of guessing and emotional Sudoku ever will.

We spend so much time talking about chemistry that we forget about something equally important: ease. Fireworks are great, don’t get me wrong. But comfort is just as necessary, if not more so, especially when good sex is one of your goals.

One last thought. I smiled when you described this as your slut era, because there’s something wonderfully freeing about dating without trying to audition every attractive stranger for the role of Future Spouse.

Don’t lose that freedom now. Casual dating doesn’t mean lowering your standards for how you want to feel. If anything, it’s the perfect time to practice trusting your own experience over someone else’s mixed signals.

The whole point of a slut era is that you don’t have to force a fit — or to accept confusion just because it’s hot. Hot is a bonus. But don’t let it come at the expense of truly enjoying yourself.

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