I dislike discussing celeb romantic interactions because it’s somewhat of a different world than what happens for the rest of us. I’ll try to discuss this in general terms that are relatable to the common man.
Pete Davidson is good at attracting physically attractive women but these interactions rarely last beyond 6 months.
@BackInTheGame78 mentioned a key reason why that is. There are regular men who are like Pete in dealings with women.
Two women (Kate Beckinsale and Kim Kardashian) were single moms who were 20 and 13 years older than he is. That’s not the best use of time for any man. Those weren't going to be sustainable in any way.
Ariana Grande & Kaia Gerber (Cindy Crawford’s daughter) were better than an age perspective. Grande is a few months older (not a big deal when both people are under 25) and Gerber was 5+ years younger. Gerber was one of the more impressive short term gets. However, it would be fair criticism that Davidson didn’t keep a hot, 18 year old around longer for a few months. Any 25-26 year old would get criticism for that. Additionally, it was a bit impulsive for him to put a ring on Ariana Grande within a few months of dating. Fortunately for both sides, the engagement broke up. In the regular world, putting a ring on a woman after less than 6 months of dating would be called AFC/beta, regardless of how attractive she is.
In considering Pete Davidson's exes, the women are either over-the-hill (Beckinsale, Kardashian) or screwed up in some way (Grande). That’s not impressive. If you value LTRs at all, Davidson’s most impressive relationship with 2+ years with Cazzie David (Larry David’s daughter). Cazzie David is cute/maybe attractive but not as hot as some others on that list during their primes. Also, she is similarly aged.
Two of the biggest keys to Davidson’s game are height, salary, and a big penis. There have been non-celeb men who have used that combination to get them some attractive women.