So, for the past couple of years, one of my close friends has had a pretty rough time with dating. It’s not that he’s bad at talking to women or clueless about relationships, but somehow he always ends up in really weird or unfortunate situations—usually through no fault of his own.

The longest relationship I can remember him being in lasted about a year, but it ended because his girlfriend told him she wasn’t feeling it anymore. For context, they got together not long after she had just come out of another relationship, so that was probably a red flag from the start.

Fast forward to 2024, and in the span of just three months, he’s tried to spark something with several different women—one after the other. Most of these attempts didn’t go anywhere. Today, he messaged a random girl on Instagram he didn’t know personally. At first, everything seemed to be going really well. A little too well, honestly.

Within five minutes of talking, she was already calling him "cutie" and dropping kiss emojis. By the end of the day, she blocked him. Naturally, he was a little bummed, even though the whole thing barely lasted 24 hours. This is just the latest in a series of interactions that don’t end well for him. There are more examples I could give, but I don’t want to go into too much detail.

The thing is, I care about him and I want to help—but I don’t want to come off as controlling or like I think he’s incapable of making good choices. I just want to help him see patterns or maybe reflect a bit more before diving into things so fast.

AITA for trying to figure out how to support him without stepping on his toes? (I would HAPPILY take suggestions on how to go about this)