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I don't want to say never - although since I'm already married I guess I can - but I doubt that I would have married someone that had been with prostitutes. And no - you shouldn't lie about it.
It would bother me, but everyone has moments of weakness or depression that may lead them down that path. Now, 20?? No. That's a bit much for me, but if it were once or twice I think I'd be ok with it as long as he's been tested for STDs and is clean.
I wouldn't appreciate being lied to about something like that. Honesty is the best policy, because if she finds out down the road it could mean a really bad, messy, angry breakup. Be honest if things get serious, but I wouldn't open with that on the first date.
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