I (28F) went on a few dates with a guy (35M) who would occasionally sleep with his very close girl friends. I've met plenty of guys from dating apps who have similar dynamics with their best friends but this is the most memorable one:

We're both ambiamorous but have different ideal relationships. I'm more experienced in monogamous relationships while he's more experienced in non-monogamous relationships. He wanted to start with monogamy and slowly open up the relationship. “It would be nice to be in a relationship, in which I can freely cuddle my gal friends platonically,” he said. As for me, I can commit to either monogamous or non-monogamous relationships, whichever works best for us. If it's non-monogamous, I wanted to practice non-hierarchical while he wanted a primary partner (Should've known we weren't compatible after learning how black-and-white our desired non-mono rel style. Please don't come at me. This was a “lesson learned” experience for me)

He was very open about remaining good friends with former FWB after the benefits were dropped. He has a big circle of friends and said they're very open with each other so cuddling is often involved when hanging out and (although not expected) sometimes led to group/1-on-1 sex. Upon hearing this, I asked about his safe sex habits since I care very much about sexual health. He only got tested 2x/yr and doesn't wear a condom with his friends because he trusts them. (But proceeded to talk about how a few did get chlamydia???) Anyways, his love language is physical touch and felt like the physical intimacy shared between him and these friends deepened their friendship. Maybe I find this intriguing because I've developed meaningful, quality, long lasting friendships without physical intimacy. I focus on emotional depth with friends and there is no sexual tension to explore in our connections. My friends are attractive but I don't have any urge to be physical because that would change your dynamic. I did feel sexual tension with 1 girl friend and she felt it too. This friend and I talked about it extensively and we both agreed that exploring that tension would change things between us.

How do you feel or what do you think about dating someone who has had sexual history with most of their best friends?