I started punting when I was 23 last year. In half of the encounters when I visited a WG for the first time, I always get asked why I'm doing this or if I have a partner. Weird? Nah, in fact I occasionally find myself being the chatty, TW I am sometimes but that's just my personality and my fault.
I don't get offended or sad about these questions because I always say I just want to try something new for once.
Maybe it's because I look young but I was told that one of the top stereotypes is that younger men are "jack the lads" and are inexperienced when it even comes to talking/relating to women without sounding like a creep as you pointed out. I hear that they don't all come across very well either, often being brash sometimes which doesn't give off good first impressions. It's easy to see why WGs sometimes just don't feel comfortable in certain situations when it comes to age of even ethnicities if we really wanted to go down another controversial route (hey, we all have our preferences at the end). But being young shouldn't be a setback most of the time if you're respectful and hygienic as they say 99% of the time.
Yes, we're all paying for a service as that's what they're here to do but as with all other customer-centric jobs out there, it doesn't hurt to be nice. Call me stupid or w/e, but I still believe that people who are rude to their waiters for will spit in their food...