I started watching DS9 from the start again today.
In the first few episodes Bashir's like a cartoon stereotype of a philanderer, like Barney Stilson or Okana.
I think most screenwriters just have no idea how to write a believable philanderer, because their experience with jocks is being pushed around by them.
I think some of that was on purpose, though. Or, at least it seemed that way to me. He seemed to get around a bit, and he was playful, but it's like he was trying to be someone he wasn't. It makes me think there's a reason why one of his favorite holographic programs was James Bond-esque. Except, he's not James Bond. Jadzia could see that right away, and I think that's one of the reasons she brushes off his advances. He wasn't ready for her yet, and by the time he was, she'd found someone else. Such is life.