You said “don’t mention the age gap” but it has everything to do with the situation you’re in; you started dating this 44 year old man when you were still a teenager and he was fresh out of a two-year engagement. Have you had a serious relationship before him? Or is this your first one? Because that’s also relevant information.

I was raised by my grandparents and great-grandparents, I usually feel more comfortable around the elderly than with my peers, I get it, but even as a 24 year old the idea of dating a teenager is skeevy to me. Having a preference for someone older than you is common, but it’s important to keep in mind why someone so much older would be interested in you who is more than half his age.

As much as you don’t want hear anything about it, this is as relevant to the conversation at hand as any other detail in your relationship.

Unless used “perfectly” every time, condoms alone only have about an 87% efficiency rating. Go to the drug store and get a pregnancy test if she’s over a week late.

They didn’t come naturally to me either! My therapist told me I was probably autistic when I was 15; you should look into that.

As an autistic person, I’ve had to teach myself to laugh more during interactions or else people will think I’m not enjoying myself. It was a strange process.