My [25F] good friend [27F] misses social cues and awkwardly brags about herself in social settings. Should I tell her this is weird and off-putting?

My friend, Annie, is a really awesome, fun girl. She's kind, fun to be around, and a thoughtful friend. But she has some qualities that I think are affecting her ability to make meaningful relationships and friendships, and I'm wondering if I should tell her, and if so, how.

The main thing is that she brags about herself in awkward ways that come across as tone-deaf, and often make the people in the conversation feel uncomfortable.

For example, one of our friends was lamenting how she wished she had bigger breasts. I pointed out that lots of chesty women wish they had smaller boobs, and they often say that it's harder to run a mile or swing a baseball bat with a bigger chest. Annie laughed, and said, "I have big boobs and I've never had a problem doing those things. I think that's just something smaller-chested women say to make themselves feel better." She clearly did not understand that this was rude, and went on to discuss how everyone should just be happy with the body they're born with.

Another example is that she frequently says she has trouble finding a boyfriend because men always "unicorn" her. She says this to mean that men, upon finding out she has traditionally nerdy/masculine interests like sports or video games, put her on a pedestal and comment about how unique she is, and she hates this. (I don't think this is necessarily why Annie has trouble getting a boyfriend, but that is probably not relevant.) She regularly laments about this in our friend group, but it comes across as a real humble-brag that sounds much less "I wish I had a boyfriend" and a lot more "it's so hard being hot and cool." I know she doesn't actually feel this way, but that's still how it comes across.

She will comment, un-prompted, on my fashion choices (e.g., "those jeans don't make your butt look good" or "that dress isn't flattering on you,"), though she will often follow up with an offer to lend out something from her own closet.

She will occasionally interrupt conversations to redirect them to something about her, usually in an awkward way that forces us to compliment her. For example, she likes to cook, and recently interrupted a conversation we had at group dinner to ask, "this food is great, but what is your favorite thing I've ever made you?" It was just a weird timing and forced us all to abandon organic conversation in order to go around the table and compliment her.

Relatedly, my boyfriend, Steve, knows Annie from law school. She actually used to have a big crush on him, and when I asked Steve why he never went out with her (she is, as I said, very pretty, smart, fun, and cool), he said it was because he was pretty off-put by this behavior in general, and more specifically, because at a law school function she kept trying to impress him by bragging about all the sex she had in college, clearly not realizing how uncomfortable it was making him and the other people within earshot. [ETA: this is especially weird, because I can picture Annie doing this, but it is also a lie. She did not have a lot of sex in college, or really many romantic relationships at all, and Steve is a pretty visibly religious, conservative guy on that front.]

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I know Annie very well, and know that she's not an egotistical person at all. She is actually fairly insecure, mostly about her romantic loneliness, and I suspect that's where a lot of this comes from. But this behavior isn't making her appear confident, it's just making everyone else feel weird. This doesn't happen very often, but often enough that it's a trend and I think it impacts her ability to form initial friendships and romantic relationships.

Annie is a good friend, and I think she would want to be told if she was upsetting people. But she's also defensive, and I'm not sure this is my place to tell her, or if it's something she'll need to learn on her own. Is this a conversation I should have with her? If so, what is a delicate way to approach it?

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TLDR: My friend is lovely and awesome, but misses some social cues and exhibits some quirks that make it hard for her to make meaningful relationships. Should I talk to her about it?

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Ninja edits for clarity/spelling mistakes.

Submitted January 30, 2019 at 06:46PM by othrwisecheetah http://bit.ly/2Tm3JIM