My partner (35m) of five years has never dated anyone older than 21 or been in a long term relationship outside of myself. Are those red flags

Hi so I am a 23f who has been dating my partner, a 35m for five years now and I haven’t been exactly happy in our relationship for the past few months. Of course I did the dumb girlfriend thing and began to overthink things and that’s where it kind of went downhill. I began to piece things together and realized that in all his relationships, his SOs were never older than 21. He has dated about five-six women since high school and two were while he was in high school so yes they were under 21 but after high school he was the guy going after the high school freshmen and having mental breakdowns over them. One of the girls was a young, work acquaintance, another a young childhood friend, and the last was a childhood friend’s little sister. The others were I believe just high school girls going to college parties. This went on until he was about 27-28 and he took a break from women but still flirted with younger girls. None of the five (the sixth girl I cannot quite remember may have been 22-23) relationships lasted more than a year. When he was 30, he met me and we began dating. He has slightly shit talked his former exes but also like...they were under 21. People under 21 in general are immature. I don’t know if he has ever stopped to realize that.

Looking at it now...it kind of seems like a red flag? The “never been in a long term relationship” I could maybe sideswipe because there are plenty of people who are older than 25 and have never been in a long term relationship, but the ages of his SOs? I may be overthinking it because I’m unhappy with him right now but it comes across in hindsight as a bit predatory. Am I being paranoid?

Edit: Also when we began dating I had to tell him to stop communicating with one of his online friends that he had been talking to for about 4 years. She was 19. The age at which he began talking to her made me uncomfortable and I told him that. He threw a fit and said I was being overly possessive and didn’t see what was wrong with him having female friends. He finally agreed and texted her goodbye, saying I had told him it wasn’t okay to talk to her and she just never responded and blocked him lol.

TD;LR My 35m partner has never dated someone under 21 or been in a long term relationship outside of myself and I’m feeling like those two things are beginning to look like red flags

Submitted May 26, 2020 at 11:36AM by screamingpossumss https://ift.tt/3c77gD8