Of course you should question his character. I mean, what kind of man tells a woman he’s casually seeing that he’s slept with 100 women? What the hell is wrong with this guy? Doesn’t he know that a man should never, under any circumstances, admit to having slept with more than fifteen women? You can be 120 years old and must still only admit to sleeping with fifteen women. Any more than that and you’re entering a world of pain—your girlfriend will make Torquemada look like the guy at the local 7-11 who’s been selling you cigarettes since you were 12.
(When possible, I don’t admit to having had sex before. This way, at least my poor performance is excusable. And I tell you, you’d be surprised how understanding a woman who is continually not being pleased can be when you plead naiveté.)
I always view a potential girlfriend’s sexual history like I would her criminal history. Get caught stealing as a minor or date a man who’s 26 when you’re 18—hey, no big deal. Hump your college boyfriend’s best friend or get a DUI—that might raise a red flag or two, but I can handle it. Have sex with the entire Portland Trailblazers basketball team (three times) or shoot up a school for orphans—honey, I don’t think it’s going to work out.
The point is that for the most part, sexual history should not be taken into consideration. But in the extreme, it is very difficult to ignore. If you are strong enough of a person to get over it, then God bless you. Me, on the other hand, I’d spend every night lying next to her wondering what names she hasn’t had sex with. (“Ok, she’s probably done a Josh. Definitely a Jim. Maybe not a Jeremiah. But probably a Jeremy. Crap.”)
One last piece of advice regardless of whether you stick with him or not: He may have told you that he’s slept with 100 women to impress you, to show you how sexual and sexually advanced he is. So throw it right back at him. Next time after you’ve made love, ask him, “So you’ve slept with 100 women?” When he replies yes, let out a dismissive and confused “Hmph” and give a puzzled look, staring deep off into the distance. That should put him in his place. “Playboy” my ass.