Most Helpful Guys
It's about whether they are really former or not. In this case he's not former. It's too recent to be former.
"I am the first girl he has had feelings for"
Or maybe you are the 21st girl who is the first girl he had feelings for.
There i no evidence that he is a former player. Wait five years. Better yet, wait ten years. In the meantime, watch his eyes. I bet those eyes are roaming, and the next skirt that catches his eye he'll be gone.
On the other hand, I'm not sure if 20 in three years qualifies him as being a player. That's not many for a player. 20 in three weeks is a lot, not 20 in three years.
There is no way to predict, but this sounds like high risk. If it's someone you want, try it out. But be ready in case it goes wrong.
"he’s super nice, genuine and respectful and treats me well"
He wouldn't be much of a player if he didn't know how to treat a girl.
I would say it's a stupid idea, but people DO change. My younger brother used to be THE definition of a player, on an epic scale. I knew he was pretty bad, but my ex told me that when he was drunk, he admitted to her that he'd cheated on every single girlfriend he'd ever had... even I didn't know that as his brother, and he's thoroughly ashamed of it now.
He's 25 now, in a long term relationship, and I genuinely can't imagine him cheating on his girlfriend. He's a totally different person now, and he has actually changed into a better person.
It will probably end badly, but it's up to you if you take the risk. People often don't grow up until they're in their mid 20's if not 30's so the risk is there, but people sometime DO change when they meet the right person.
Most Helpful Girls
If you like him, date him. We all have sexual history and as you get older numbers stop mattering. Plus him having experience mean he should be pretty good in the sack and will be able to give you orgasms. You don't know how great sex can be until you have been with a man who has been with a few women. Trust me.
Sure. people can change and have regrets. BUT!!! You need to play it smart here. All you have is what his is saying. No sex with him for at least 3 months (and preferably only after you both have discussed you are in an exclusive bf/gf relationship). Players will not stick around too long if they are not getting what they want fast enough. As there are others out there that will give them what they want faster. Hold off on sexual activities!!! See what he does then. A true man that is not a player will respect that, and stick around.