New boyfriend is a teacher and makes unsettling comments.

6 months: this means he's comfortable with you, but it sounds too comfortable - he's probably starting to see you as someone he can say the same stuff that he would to his bros/friends when he was in his 20s. And if he's a normal early-30s guy, he's probably not hanging around his brosephs as often as he used to, because life/job/etc, and he misses that. But you are not his replacement friend.

Gross as it sounds, plenty of college dudes and dudes in their 20s joke about this sorta thing, and 99% of them don't even come close to going through with it. Lots of my friends (and I) went to Catholic school in the midst of all the pedophilia scandals - we laughed about it a lot, because it was f*cked up.

He's only said it twice in 6 months; I'd certainly bail if it was twice in 3-4 dates.

Sounds more immature than creepy, IMO.

Don't insta-dump him right now like some folks are suggesting. But be stern and talk to him: "hey this isn't funny; it's a big deal". See how he reacts. If he fights you on this (even the slightest bit), then you can bail.

At the very least - for yourself: use this as an opportunity to grow and gracefully handle a conflict - if you insta-dump him without even confronting him, then you lose that opportunity to grow. GL.

/r/datingoverthirty Thread