Is it a bad idea?

I’m dealing with a situation that’s been on my mind a lot and I’d appreciate some outside perspectives.

I met this girl through someone who used to be a very close friend of mine. They were together for quite a while before eventually breaking up a few months ago. Some time before their breakup, her and I started getting closer as friends because we realized we shared a lot of similar interests when it comes to work and future goals. Naturally we started talking more and spending time together.

After their breakup, we kept getting closer and eventually started seeing each other a bit. I genuinely like her and she shows interest in me too, but there are a few things that make me unsure about the situation.

Not long after the breakup, she ended up sleeping with an older guy. She says it was a mistake and that she regrets it, but when the topic comes up she sometimes smiles or laughs about it, which honestly makes me feel a little strange and hurt.

Another thing that’s on my mind is how our connection started. Since she originally knew me through her ex, part of me wonders if this type of situation could repeat itself someday. I don’t know if that’s a fair concern or if I’m just overthinking.

There’s also the moral side of it. Growing up I was always told that dating a friend’s ex is kind of a bad move. The guy she dated used to be one of my closest friends, although over time we drifted apart and aren’t really close anymore. Still, it gives me a bit of an uneasy feeling.

Our personalities were always very different too. I’m a pretty calm and passive person, while he was known for being more confrontational and causing problems. I think that dynamic probably affected their relationship.

So I’m feeling pretty conflicted. I like her, she seems to like me, but I keep wondering if getting deeper into this situation will bring more good into my life or just create unnecessary stress.

Has anyone been in a situation like this? How did it turn out?