-I had met this HB (HBGlasses) the other night while watching some street performers strumming some shit songs on the sidewalk. She happened to be friends of a friend. I teased her by telling her to take part in a dance-off. She laughed and told me her name was HBGlasses. Told her I was leaving, kissed her on the cheek, got her number.

We try setting up a date a few days later. Plans fell through until later in the evening. She said that she and our mutual friend were going to a diner. I was already out with my wing, so we decided to roll will. HBGlasses' friend bailed so it was basically just an awkward third-wheel situation. He spends the rest of the night talking over everyone else about uncomfortable things like his cat dying, trying to flirt with HBGlasses by making awkward jokes.

I apologized to her, but she has steered clear of me since.

-Me and my wing (the same wing from the last story) were out at a bar, hanging out with our buddy Mickey. He sees a girl (HBSingleMom) that he's been into and her friend (HBCurlyQ). So he goes in and breaks the ice, I join in after about 5 minutes. So I start chatting up with HBCurlyQ about birthright trips to Israel.

I look over at my wing and he's sitting there looking down, sighing. HBSingleMom has her arms crossed and is looking at the crowd in the bar, wearing an annoyed expression. I try to soothe things over by just trying to talk to her. HBSingleMom was friendly enough, but then, out of nowhere, her old co-workers interrupt and scoop up both girls.

To this day he just claims that she just "wasn't feeling his vibes" that night.

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The ultimate lesson of psychoanalysis is that human life is never "just life": we are possessed by the strange drive to enjoy life in excess, attached to a surplus which derails the ordinary run of things.
-Slavoj Zizek

First, have you discussed this with the wing?

Second, there must be more wings in your location that you get on with.

Yeah, my wing is one of my best friends and is the guy who introduced me to game. So I've spoken with him about these things. I have a lot of criteria for friends in general, so a wing has to fulfill quite a lot. The town I live in doesn't really have much to offer in terms of both friendships and romantic pursuits. Thinking about moving away completely.

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The ultimate lesson of psychoanalysis is that human life is never "just life": we are possessed by the strange drive to enjoy life in excess, attached to a surplus which derails the ordinary run of things.
-Slavoj Zizek

There's some nights where you're just off. You've obviously been the same yourself. It just happens and you have to let it slide. However, the inappropriate topics of conversation are generally a huge tell of just how insecure the guy is(That or he's a psychopath or suffers from some form of autism).

I've had it myself where a wing says the most stupid of things to women even though you know you can nail these women... this one guy would fuck it up and say something stupid related to STDs or kicking dead dogs or some stupid shit like that then genuinely laugh as they would walk away disgusted or freaked out. The trick with these guys? If it's a constant issue... Just don't use them as wings. Seriously, it's them... When they open their mouths and say those stupid things it's them. You have no control over that so just head out with them and don't take the night serious. If it just happens once in a while then just consider an "off" night for him.