I'm a bit of a cradlerobber, we'll say, and I've hit on plenty of boys in their late teens and early twenties. Initially they seem really flattered and claim that age isn't an issue, but they sometimes seem to have a hard time moving outside of the fantasy realm...I can think of a situation last year where I had a great pizza date with a 21 y.o. who seemed eager to see me again, but had cold feet when I called him proposing fooling around at my place. Our mutual friend confirmed that he was definitely interested..eventually he got up the nerve and called me back, but by then I'd lost interest. I don't think he was used to the lack of pretense people usually go through to get laid, but it wasn't because he was looking for something serious - I think a lot of young dudes think "wow, it would be awesome if some girl told me she wanted to suck me off right now," but have no idea how to behave when it actually happens. One interest told me I was a hottie and seemed awesome, but claimed that he was intimidated by all my life experience, and that he couldn't begin to measure up to me in that respect. I didn't expect him to have as much life experience as me - it was enough that he was doing really interesting things with himself and on the right path. I guess what I've noticed is that when there's more than a five year age difference, boys really like the ego boost of having a "cougar" or "puma" expresss interest, but are often unsure how to handle our forthrightness and would prefer to relegate us to masturbation fodder. I'm usually assumed to be in my early or mid-twenties, too, which makes things especially tricky - the youngsters are sometimes interested until they hear how old I am, at which point they back off. It's ridiculous to me b/c it seems like it'd be the best of both worlds - someone who can pass for an age peer but has the experience of having been around a bit longer. So, young guys, what do you think? Would you mess around with a woman five or ten years (or more) your senior? Would you seriously date one? Would you be freaked out by what your friends or family would think of the age difference? Are you concerned that she'll expect a level of seriousness you can't commit to at your age, or delighted by her ability to ask for what she wants? What do you think the advantages and disadvantages of being "the younger man" are?