One friend and I had a mutual crush and my friend would constantly try to manipulate the situation to be in his favor. Ironically, it worked against him more often than it worked.
The first time, he invited me as a blind third wheel to the movies without telling me she was going to be there -- the two of them showed up dressed in nice casual clothes, and I show up in a T-shirt, jeans, and lopsided hair that was halfway done, halfway-bedhead. However, the funny part was, at the end of the movie I made her laugh because she had been self-conscious about hers, and I compared it to mine and said, "Hey. It could be worse. It could be like mine is right now. Mr-Bedhead-Looking-Guy-In-His-20s." (Paraphrased). Later that night, she invited me to a campfire thingy with a bunch of her friends while the other friend remained uninvited. That always stood out as ironic to me.
The second time, she arranged a hangout at her place with a bunch of us and I was working until late that night. My friend (which I didn't fully realize until later) started texting me "non-chalantly" about it, to which I replied that I wasn't sure if I could make it. The moment I said that, he apparently told her that I told him that I wasn't coming that night. HOWEVER, the funny part was, since he kept me in the dark, I showed up with my guitar and suddenly she was like "OMG you came! And you brought your guitar!" In a Professor Snape-like voice, he looked at me and said, "Oh. I thought you said you weren't coming." We all watched a movie and I played some songs and we shot the shit until, like, 2:00 in the morning. It was fun. It wasn't until she told me what my friend had said that I suddenly realized the bigger picture.
However, after all was said in done, the funniest and most ironic thing about that whole charade was that she married a completely different friend than both of us! I was kinda heartbroken (not gonna lie) and my other friend was bitter about it, but in the end, I think it worked out for her, and that's what mattered most to me.
But yeah, two "My friend's kind of an asshole" moments. ;)