This is why people hate Gen Z. Kidding (sort of).

mrsconn23

Dear Prudence,

I’m the eldest of two—an older sister to a younger brother. We’ve always been thick as thieves. Even though we’re a few years apart and look completely different, people often refer to us as twins because of how close-knit we are. We’ve always understood each other, even though our personalities are a bit difficult to read at times for others. This leads to the problem: We’re both in our 20s and he has his first serious girlfriend post-high school.

She’s a nice, personable woman, they’ve been dating for a year, and recently she’s making a HUGE effort to be my friend separately from her relationship with my brother. All of that is great and normal, but it just isn’t working for me and I don’t know what to do about it. We’ve hung out a few times because I’m bad at saying no to decent people, but our personalities don’t align enough for those interactions to have been truly enjoyable. I love spending time with my close people, or even in crowded events where my attention and energy can flow, but spending hours alone with someone I just don’t feel relaxed around is more than I can sustain long-term. I am a social person, and I enjoy her in a group setting; I’m just not convinced we’re ready for the type of relationship she wants and I don’t know what to say when she tries to make plans.

I also can’t help but feel like her attempt to be friends is motivated by a desire to understand my brother better or to gain my approval of the relationship. I can understand how a romantic partner would think my opinion of them would matter to him and she’s subtly asked questions that I’ve evaded, because he and I don’t share each other’s secrets, ever. I understand why she would want to have a friendship with me, and I don’t disapprove of her and my brother’s relationship in any way, I just don’t feel compelled to keep up a friendship that doesn’t feel natural. My question is: How do I either rise to this occasion and realize I just need to figure out how to be her friend or how do I let her know that this is too much, too fast for me? I don’t want to hurt her feelings, I just feel like I’m compromising my own boundaries to not rock the boat for her or my brother and I don’t know if I can/should sustain that.

—Overwhelmed in Oregon

short+sassy

I'm always a fan of "having a busy schedule".  Since it sounds like the LW would be open to some socializing, I'd recommend she invite this woman out for one-on-one time that is a limited amount.  Like going for lunch, but the LW needs to go straight to (insert errand/something else) afterwards.  The LW could also invite her to group events, since she enjoys her company more in those settings.

But I feel like this is one of the few instances where having a serious conversation about boundaries is a bad idea.  The LW can give that same vibe without hurting her feelings by saying "no" to a lot of invitations, but "yes" to a few she would enjoy more and/or doing some invites herself. 

charlotte989875

Maybe it feels awake and because you’re making some wild assumptions (that she’s trying to glean secrets about your brother) or reading something into her wanting to be friends (that she’s seeking your approval) rather than she’s just trying to get to know you. 

They’ve been together a year. That’s more than a casual thing. So either find a way to hang out, or say you’re busy when she asks. You don’t have to be best friends with, you don’t have to hang out 1:1 either, but there doesn’t seem to be anything overwhelming or boundary crossing about her asking to hang out. You can just simply say no. 

mrsconn23

This email makes me think of that one Friends episode (The One With the Inappropriate Sister). I literally can't tell if LW is reading too much into the tea leaves or not with the GF. 

The letter comes off gate-keeperish and also the whole, "I need to feel the right vibes."  Dude, calm down.  If she asks to meet for coffee and you're not feeling it, just be all, "Sorry, I'm busy."  But I don't think she's got some insane plot to infiltrate y'all's super special sibling relationship that no one else can understand (*eye-fucking-roll*). 

Also, you could try to plan to have dinner with her and your brother together so it's quasi-one-on-one time, but he's there as a buffer.  Just let her clean up his crotch if he spills something. 

short+sassy

I'm reminded of Louise's "friend" Millie from Bob's burger.  I love her character!  She is so over the top with her cringe and it's hilarious.

levioosa

charlotte989875 said:

Maybe it feels awake and because you’re making some wild assumptions (that she’s trying to glean secrets about your brother) or reading something into her wanting to be friends (that she’s seeking your approval) rather than she’s just trying to get to know you. 

They’ve been together a year. That’s more than a casual thing. So either find a way to hang out, or say you’re busy when she asks. You don’t have to be best friends with, you don’t have to hang out 1:1 either, but there doesn’t seem to be anything overwhelming or boundary crossing about her asking to hang out. You can just simply say no. 

BIL B dating someone who could be a ton of fun and who I thought was a better friend, but SIL and I realized that a lot of our "friendship" was her trying to talk about BIL B or trying to find out more info about him. Sure, there was a lot of other stuff too that we talked about, but it really brought down the friendship and it was easy to see. They broke up and it got even worse because we'd meet up to hang out and she would still try to talk about him and ask what he's been up to. To the point where the last time we tried to meet up, SIL and I said that was it for any of our effort towards the friendship. 

So maybe LW is reading into it too much and needs to chill. Or maybe GF is being that way. Who knows. But I don't understand why she can't try to hang out more in a group setting and just let any friendships grow naturally.

MyNameIsNot

This much overanalyzing makes me want a drink. Or it makes me want to make LW a drink. 

Casadena

I've been with H for 14 years and i still feel weird being one on one with his sisters for extended periods or frequent occasions. They're great, i love them a lot, but we've never been friends that way. LW, just say you're busy or ask to hang out in groups. You're making this a way bigger deal than it really is.