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