Well there's 2 sides to that coin (morality/honesty aside):
On one side, unless the girlfriend is herself a virgin, she WILL tell if the dude has never done it. You just cannot fake something like that. Any attempt to bluff will blow up in his face like when Andy tried to bluff at the poker game ("bags of sand" anyone?).
On the other hand, any woman dating a 40 year old for anything but his money will be expecting a 40 year old to be experienced (remember Helen HUnt's rant to Nicholson at the end of As Good and it Gets: "You're too old not to know, and I'm too old not to notice!"). Unless he's got a hell of an excuse (Mormon or some other religious cult) he'll come off exactly like Andy did at first: a weirdo at best and a serial killer at worst.
So a real life 40 year old virgin BETTER be dating another virgin or have 10 inch thick skin to endure the ridicule/explaining he's in for.
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