As always, in case you can't read the text, it states:
loose sweats
older looking for older who enjoys fun times
The simplicity. The mystery. What's being straight up said and what's being implied. Let's dive right in with our questions.
Why "loose sweats"? Is this supposed to be a reference to an erection in sweatpants? Is this person just stating that their pants are getting a little big on them? Is this person looking to only hook up with people who wear loose sweats? ARE THEY EVEN TALKING ABOUT SWEATPANTS?? These days there's no telling what's slang and what isn't unless you're part of the specific community it's relevant to.
"older looking for older who enjoys fun times" This person clearly hates specifics. Older...? What? The pansexual population, although wonderful, is relatively low. You'd think this person would want to specify in order to attract their intended demographic. Also, what constitutes, "older," cuz I'm 27 and I feel every cell in my body dying.
But maybe this person isn't looking to hook up at all. Maybe they just want someone in their age range to hang around in sweats with them all day and play Checkers. Weirdly, that sounds feasible. But it's Craigslist so...