Not a confidence thing really, I'm confident on dates, I've dated so many.. Some girls are really annoying about that, it's almost harassment, they want to know. If I thought I was too old I wouldn't approach and date girls in their 20s. What I believe doesn't matter, it's what they believe that matters, THEY decide if they are going to sleep with you. When they ask me my age I ask them how old they think I am, they say 30 for example, then I say then I'm 30 and then they keep asking until it become annoying, they have to know because for them it's important. I've noticed that if I tell them right off the bat like it's nothing, like I'm telling her my name, it doesn't work. During the date they don't mind about my age, but the next day when she wakes up she is going to start thinking about me and do a mental list of pros and cons to decide if she is going to see me again, age is a con, not a huge one but still a con. I don't care about being 35, but I care about the fact that it plays against me. Actually I have no idea how to deal with that (any suggestions?). Telling her the truth right away, lie and keep lying, play games and don't tell her, date older women (fvck no)? I study at the university with 18-19yo girls, they send IOIs all the time, but I'm just too old, they may fantasize about the older guy, but they will not act most of the time. Psychological barrier. Like I said, it can happen, but you shouldn't wait for that.
It's my opinion only, but I doubt a lot of regular guys in their mid/late-30s get laid with a lot of early 20s girls, unless they look like god, drive super cars and make a lot of money so they can support the lifestyle girls in their early 20s want. If you don't have that, those girls have options, younger options.
Come on man, those actors, singers whatever are superstar, they have status money reputation talent. They live in another reality, not our reality. I'm pretty sure Jack Nicholson had a blast when he was younger but now he doesnt fvck hot young girls in their 20s in pretty sure, maybe the gold diggers or the ones who want a sugar daddy.