Why does this guy keep trying to set me up with his guy friends?

[Anonymous]

My friend from work wanted to go out with her guy friend from her school. They were never super close and she doesn't like him as more than a friend, so she thought it would be awkward for her to go somewhere with him alone. So she begged me to go. I also thought it would be awkward because they were flirty with each other (despite not liking each other) and I thought I would be the third wheel.

We ended up hanging out with him at the pool and the mall, just us three and he asked if I was hanging out with them later, then told me I was making up excuses then he started begging me to go hang out with them later that night, I had no idea why. Maybe he figured she wouldn't go if I didn't. I told them we should just go to something simple like a movie but they wanted to do something else and he promised he would go to a movie next week and see anything. They were so persistent.

So I hung out with them that night but he brought along his guy friend, which made it feel like a double date. I was not attracted to the other guy whatsoever, yet he kept trying to get me to get with him the whole night. It was so awkward! I previously danced with his guy friend before at a club but only because I was standing there as the third wheel again.

My friend told me he felt bad and was testing my limits. He probably felt bad that I was going to be the third wheel so he tried to set me up but I don't understand why he was "testing my limits"? He flirted with her all night so I just hung out and made small talk with the other guy. Then he teased me frequently too about getting with his friend and just about anything.

Why did he try to set me up with a guy who is clearly not my type and he knows? Why was trying to test my limits?

[jesshkah]

whatever "testing your limits" was, is a stupid concept. I hate being tested, and but yea, you're probably right, he felt bad that you were third wheeling and he figured that since you danced with the guy you liked him. Some guys are really thick lol.. like he might have thought you didn't mean it when you said your seriously wasn't into his friend. Maybe he thought you were just scared of admitting that you like him or whatever. "test your limits".. maybe test how much you really liked hanging out with them? Test how much you were willing to talk to the other guy.. that's just a weird phrase to use.

[Asker]

I thought it was strange as well, my friend told me "Thats what guys do, they test your limits". I have no idea what she means-she probably just said it to come up with an excuse as to why he keeps trying to set me up with his friend. He was just so pushy. We went to a hookah bar and he kept telling me to shotgun hookah with his friend and I told him no and jokingly told him to do it. He said if he does it then he wants me to do it because he wanted to see me do it. I was dragged into going.

[jesshkah]

Lol she probably didn't know what she was talking about either and just made something up.. pushy guys are annoying.. you gotta just stop joking at some point and be like "I'm seriously.. not interested."

[Asker]

Yeah I told my friend to tell him that I am not going to hang out with them next time. After we left last night, I told her I was mad and that I am not doing that again haha, hopefully she passes the word on and lets him know, no more set ups!

[martyfellow]

He's interested in you and wants to know if you're interested in him, and for some reason, he doesn't want to approach you directly...so he's setting up these group scenarios. I don't know what yur history has been, but he may feel pretty sure you'd reject any direct request to do anything as a couple.

[Asker]

I mean, he did tease me a lot and look at me a lot.But he also flirted with my friend a lot too, so he could just be playing. My friend told him I was a good girl and so he wanted to see if he could get me to do something I normally wouldn't, but I'm stubborn so nothing worked. Also, he told our mutual friend before that he wasn't into me or wouldn't date me or something is what she told me, so I don't know I personally think he is attractive but I don't know if I should waste my time or energy on him anyways lol

[martyfellow]

I still think he's too shy to admit he's interested in you..thinks you'll reject him!

[Asker]

I find that funny because he is a pretty cocky, overconfident guy-but I can kind of see it. I'm pretty shy too and some of the guys I talk to tell me they were surprised I talked to them. The last guy I was with, we talked for 6 months but he always still told me he felt like it was a one sided relationship, and he jokingly said I was only talking to him for so long so I could use his pool. I don't know where guys are getting this from but I must be coming across as a mean girl haha. Will he ever not

[Asker]

be shy about it? Or is there anything I can do to show him I won't reject him (without making a fool out of myself haha). If that's not the reason I don't want to act like it is lol.

[martyfellow]

If you want to know, confront him, ask him if he's too shy to approach you in a direct way!