10 years ago in my early 30’s, I spent a while running through a bunch of 22-24 year olds. It was fun. We didn’t have much to talk about though so actual dating fizzled until I met the wife who was right at 30.
even then I felt too old to juggle multiple girls that young.
My finest era was 6-7 years ago at age 30 when I was dating three girls in their 20's at once (25, 27, 28 iirc). All attractive with completely different looks, all had very different personalities. A submissive Puerto-Rican, an aggressive half-asian from Texas, and a slightly-nympho redhead of Scottish descent. Almost added a fourth (a gorgeous 24 year old Jewish girl) to the harem but I messed up with her on the second date by getting inebriated and inviting some friends to the bar where we were like a blithering idiot.
Anyway things went great with the other three for about four months or so but I lost all of them within the span of one month to various factors, some my fault, some not. One wanted me to be monogamous and I said no, one was starting med school, one adopted a dog and it started taking up most of her time. In any case, they were all great. I was honest with all of them that I was seeing other people and it worked out fine, except for the one who eventually demanded monogamy. One time I hooked up with all of them in one 24 hour span. Was with the Texan on Friday night until like 4 AM, then slept half the day, then the redhead invited herself over and I was with her all afternoon, then she left and I had like an hour to rest before the Puerto-Rican came over and I was up late again with her.
Still my finest moment and I'll probably never top it because I just don't have the energy or stamina for that kind of playboy lifestyle at 37 so I doubt it's coming back any time soon.
Edit: Also, you can learn a lot about yourself by dating multiple people at once, I found. Each of them challenged me in a different way and it was pretty different from just dating one person for a while and becoming a "certain way" around them all the time. A girl I know from my hometown is apparently in a "poly relationship" with five guys (gross) and says the same thing, that it helped her figure out who she was since she forgot while being with the same person for a long time.
PS: This post isn't thread-inappropriate because one of the three girls was a teacher.