r/Advice•
Lil_pp_87

Weird night out with my ex-step mom?

Okay, this isn’t some wild situation or anything crazy where we ended up hooking up. But it did happen — and recently — and I don’t know what to think. I don’t know if I did the right thing or if I might’ve missed my chance…

So earlier this week I was home around 9 pm or so when I got a text from my “step-mother.” Technically she was my stepmom, but not really — she and my dad aren’t together anymore, and even when they were, we barely talked. She hits me up asking if I can walk with her to a family member’s house to pick up her car, cause it was late and dark, obvious reasons I couldn’t just let her go by herself,I end up going.

As soon as come downstairs I see her, I can tell she’s a bit hammered. She tells me she has booze and weed with her if a wanted some, I agreed. We go to get her car, and the whole time she’s joking with me, being playful in this way that almost felt flirty. As soon as we get in the car, she brings up — more than once — that she “dropped a bunch of condoms” around where I was sitting, in case I found one. No explanation, no context. Just mentioned it just to have that be known and moved on.

Then out of nowhere she says we should go to the beach. It’s almost 1 AM at this point, but I say yes, when normally i say no, but it’s her so…🤷🏻‍♂️

Nothing crazy on the drive there — just more teasing and random comments that had me wondering if she was actually flirting with me or if that’s just how she talks.

We get to the beach, smoke, drink, talk, walk on the sand. Honestly, it felt like I was hanging out with someone my age. She doesn’t look much older than me, and the vibe between us felt like we were actually into each other.

Then she gets me to strip down and get in the water. Meanwhile she’s throwing these little teasing comments, saying she wants to get in too but she’s wearing a g-string and “forgot she had that on underneath,” asking if I’d have a problem with her going in like that.

I’m standing there, literally a virgin, not knowing how to act because the whole vibe was wild. Everything — the timing, the way she was talking, the situation — just felt unreal. And it’s my ex-stepmom, so this wasn’t something I ever expected to happen.

And the thing is… I always had a crush on her back when she was with my dad. Honestly, most of my friends did too. She was that type. And now here I am at the beach, while she’s undressing behind me telling me not to peek, which just made everything feel even crazier.

She even warns me she might look topless because her bra is see-through.

We get in the water — me in just my underwear — and I couldn’t even make eye contact with her. It’s pitch black, just the two of us, basically almost naked in the ocean.

Nothing happened, other than obvious flirting. But she had already been drinking, and I wasn’t far behind her, so I wasn’t going to try anything while she wasn’t fully sober.

We get out, and she tells me to strip completely naked to put my clothes back on. I swear she might have peeked — she easily could have, and I would’ve never known. I gave her one of my shirts, we left, and got some food.

On the drive back, she starts saying out loud how she can’t go straight home because she’s too messed up, talking about how she wishes she could go to a motel instead so her family wouldn’t see her like that. Meanwhile I’m sitting next to her saying nothing, because I didn’t want to come across like a creep who suddenly wants to sleep with his stepmom, I mean what could I have said to that?

We both ended up just going to our own houses. Nothing wild happened after that.

My theory is she knows exactly how she comes off. I don’t think she has in mind sleeping with me, but I think she enjoys teasing me and watching me get flustered. Maybe that’s just her personality — friendly, playful, naturally flirty. Maybe she talks like that with everyone, Yes, I’ve known her for years, but it’s different now when you’re an adult and she’s just being her actual self around you, so you actually get to know them.

I don’t know. The whole night felt weird as hell, and it hasn’t left my head.

Did I mess up?

Was she clearly sending signs that she wanted to fuh…

Or did I actually do the right thing by not trying to pursue anything with someone who was clearly intoxicated — because realistically, if something had happened, the next day once everything wore off, it probably would’ve been terrible post nut clarity?

Posted Dec 6, 2025, 6:28 PM UTC

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