I started dating my best friend’s brother

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Meredith,

I have been seeing my best friend's older brother officially for four months now. We were hooking up for about six months a year ago, but I cut things off then because it started to seem more serious to me and I just wasn't ready to tell my friend about it. I felt sneaky and gross about ultimately hiding things with him from her.

Recently, I told her everything. I can see a future with him, as his actions match his words and we just click. Since COVID-19 hit, we have been spending a lot of time together, but I still make time to see my best friend often. She gets standoffish and shuts me out if I talk about her brother and the relationship – or if he so much as posts a picture of us, she takes offense to it. (For example, I had lunch sent to him and he posted about it and she sent it to me asking why I didn't send her lunch.) It really makes me feel conflicted. I love both of them so much and do not want to lose either.

How do I bring this up to her? She is the type of person who's stubborn and really suppresses how she feels, so an actual conversation about everything could be really difficult. I'm trying to do the right thing here, but it will be difficult if she constantly makes me feel like I have to choose between the two of them. I feel like each of them has a hold on each of my arms and they're constantly pulling me in each direction. How do I handle this?

– Conflicted


If you're sure that a big conversation with your friend would be counterproductive and cause more conflict, do your best is to be as honest as possible during these individual moments of negativity and jealousy.

She asked why you didn't send her lunch, and I hope you said, "Because we're not dating." I also hope you explained that you celebrate your friendship with her all the time. Of course, those moments look different than they do her brother. Maybe they're harder to post on social media.

Go for extreme clarity. As in, "Maybe you're just kidding when you say the thing about lunch, but I hope you know that this can't be a competition. I want to be able to show one of you how much I care without the other feeling slighted."

Please remember that this relationship isn't new to you. You were hooking up with him a year ago, so this is more about picking up where you left off and making it serious. If you really told your friend everything, she's making sense of that news, accepting the history (and by the way, because of COVID-19, this might be a weird time for her to have to process anything).

She's also figuring out that this does change your relationship with her. Please don't pretend it doesn't. Talking about significant others takes on a whole new tone now. It's not all bad, but it's different. She might not want to hear certain things about her brother. Give her some time to get used to this new dynamic.

Do not assume the worst of anyone as they adjust. Ask her about her boundaries and be clear about yours.

– Meredith

Readers? How would you communicate about this? How long should it take for the friend to adjust to the new dynamic?