So I’ve (32F) known this friend (27-29m) for about 7 years. He’s never straight-up hit on me, but it’s always kinda been obvious he’s had a crush at different points.
Years ago he sort of asked me for nudes in a joking way and I was like “yeah for $35 lol” and he actually sent it. I laughed and was told him..”why would I ever send you nudes?? And for money? Bfr” We both laughed, I kept the money, end of story.
We barely talk when I’m in a relationship, but I’m single right now and lately he’s been trying way harder to talk to me. Texting more, checking in, etc.
For my birthday he sent me $100 even though I kept telling him not to because it felt weird and like it came with strings attached. Like now I feel obligated to reply to him all the time.
He keeps making “jokes” about how I’m never the one to text first. Sometimes I don’t respond for days or don’t even open his messages and he still keeps trying to keep the convo going.
I know he’s really lonely and I’m pretty sure he’s never been in a relationship and he’s still a virgin. I feel bad because I don’t actually want anything more than a very low-effort friendship with him.
Now I feel kind of crappy for accepting the money because I know I’m not going to suddenly put in more effort just because he sent it. I haven’t even spent it yet… but I do have my eye on a Kindle lol.
So… AITA for taking the money when I know I’m not going to give him more time or attention?
Edit: he knows I don’t date his gender. I’m not sure how I’m leading on.
I’m obviously not innocent regarding my past behavior, but within the last 4 to 5 years, I have not given him mixed signals or done anything for him to think money will improve our “friendship.” I repeatedly asked him not send/buy me anything.
I know yall want me to hold his hand but he is grown.
You’re leading him on. YTA
ESH. You both sound like assholes.
I mean no.. but also stop telling him to send you $, or hinting at it being a way for him to get something from you. The fact that you feel bad, makes me say NTA. However if you didn’t feel bad at all I would say YTA
tldr, NTA but stop engaging in this behavior or at the minimum flat out tell him you dont reciprocate the feelings he has towards you.
Yes
You should not have kept the money, and you need to make it clear you can’t be bought.
ESH.
You need to tell him that no, you are not interested in him and no, you are not going to send him nudes. Period. You should also return his money.
He sucks because he’s borderline harassing you and trying to pay you for nude pictures.
seems icky. Slight TA because you keep his money. Just give it back. Kinda eew.
He asked you for nudes, you said for 35 and he sent it to you… That is directly hitting on you. Send him his money back, stop leading him on, end the friendship and focus on your relationship and actual friendships…
Going forward, YWBTA for deliberately using him. Also, its really not a good idea to encourage guys like this.
ESH. Don’t take the money. It makes him feel a hope of a connection to you that isn’t there.
YTA
You are flat out taking advantage of the dude.
YTA you need to be honest with guy and let him know clearly that a relationship isn’t going to happen.
Definitely should not have kept the money at any point.
Don’t accept the money. It could lead you into some massive trouble down the road if/when the guy lashes out at you for not reciprocating or starts stalking you or worse because he feels entitled.
Its obvious you both are having boundary issues. You both have set up a relationship where you feel that you owe him and he feels entitled. But to what? It puts you in a dangerous situation.
People like this, who don’t have good boundaries can slip further and further into dangerous territory. I just really don’t recommend it.
Aside from safety concerns, ESH. You two put yourself in this situation. Him by sending you money repeatedly. You by accepting it. You both are putting yourself into an unhealthy dynamic. Best to stop.
INFO
Ok, but has either of you dragged this mess out into the sunlight?
It appears you both kind of know what’s going on and just …. keep cycling through it? You are single, he ramps the attention up again, then around you both go again.
Has either tried just lying the cards on the table and clearing the mess away?