Are we both just too afraid or is he playing?

[Anonymous]

This guy, I'll call him Tyler, and I been flirting for several months now. Well, we have talked before but we aren't close and we only flirt with our eyes. Recently things have escalated. His friend caught us having intense eye contact -- Tyler refused to look away from me to reply to his friend. Now his friend always looks at me whenever they walk by.

This Valentine's, I asked Tyler's friend, Alex, to give him a chocolate courtesy of me. The next day, I realize Alex probably gave the chocolate in front of all his darn friends. Why? Because his friends whistled and cheered at me only when I walked by (but Tyler wasn't with them). And when I made eye contact with Tyler, (he has never done this before but) he lowered his head and was blushing hard.

The issue is that he has approached me before and I have accidentally rejected him. Like holding a gay friend's hand while we were flirting (I don't think Tyler knew he was gay), he was trying to talk to me but I had headphones on and I thought he was talking to someone else, he had his arm touching mine while walking once, etc. I thought that since he rejected me asking him out to lunch (twice a long time ago), maybe he isn't interested.

I don't know how to talk to him when he is surrounded by his friends, and me surrounded by mine. Most of all, I am afraid that he is just playing with me. What should I do?

[spartan55]

I don't see where he would be playing with you at all. One of you has to sit down at big table and TALK to the other. And stop with the go-between stuff... not a good look.

[Asker]

Not sure. Some of my friends told me he might be a player and some told me that they "have a feeling" he is. Question, by go-between, do you mean by the strange way I asked his friend to pass the chocolate? Why is it a bad look? Will admit, I'm pretty young and I think I'm immature and I ended up doing that out of habit.

[spartan55]

That's exactly what I meant by a go-between. Why is it a bad look? It shows major immaturity, and that you can't be taken seriously. How is that appealing to anyone? Many guys would be completely turned off by that move and immediately crossed you off their list. (I probably would have laughed tbh)

"Some of my friends told me he might be a player and some told me that they" have a feeling he is"...
If you can't understand how immature that statement is then I really think you shouldn't be dating at all.
Second information not even based on facts, yet you have labeled this guy a 'player'? Seriously?
Would you like it if a group of dudes just arbitrarily decided you "might be" a slut. Or they "had a feeling" you were a slut? You wouldn't like that too much, would you?

[Asker]

That's why I decided to ask here. It's understandable that you would laugh at it, as your age range is done with these sorts of children's play. Go-betweens don't actually work in the adult world.

I do want to address that I understand how immature it is to paint the guy as a player. The issue is that many of my friends are telling me dumb generalizations like "he is a jock, he's probably a player". My rational brain tells me that if many people tell me this, maybe I have to trust the data. I have to admit that it is nonsensical -- as me and all of my friends used to be on a sports team as well.

I had also considered the guy's perspective, what if my accidental rejections made me come off as a player as well? Also regarding him being a player, I was scared because his ex girlfriend's friend came up to me and suddenly started talking bad about him. She said that his ex was the one who broke up with him, so I don't see why she has an issue with me dating him. (I was just scared that some random strangers would hold a vendetta against me for dating him). Also, they would not describe in detail why he was bad. But since the current world is so wary of things like MeToo and feminism, I wondered if I "had to believe" them.

I don't mean any harm. I'm just genuinely confused by the conflicting perspectives. But personally I still think he seems to be a nice person. Thank you for your wake up call though.

[spartan55]

Well hopefully you talk to him some more, and a romance blossoms.