My sister Lydia has been dating Jamar for 2 months. I live with her so I’ve seen him at home before a few times. He started working where I do 2 weeks ago. Last night, Jamar and I were working a late shift when I got a text from Lydia saying “I think Jamar’s phone is dead. Please tell him that I am very tired and would like to sleep now but would like to see him in the morning. Also, please bring home a burger for me if you can.”

I talked later to Jamar and relayed her message. He asked me “What time does she want me to come?”

I said “I don’t know and she’s probably asleep now. Text her in the morning or just come as early as possible. Or if you want, come hang out with me tonight and surprise her in the morning.”

He agreed. There was a long drive in a snow storm and I enjoyed our conversation tremendously. When we got home that night, we saw Lydia asleep on the couch in her formal attire from work. She got up and said “Hey, I’ve been sleeping here all night. I’m surprised you got here before I woke up.”

Jamar said “It’s still night. I was gonna chill with your bro and surprise you in the morning but I guess you up.”

Lydia said “I wouldn’t mind you coming to my room right now if you’re down… or up.”

Jamar said “Let’s go!” and off they went.

I found myself thinking that I was a little bit disappointed to have not gotten to spend more time with Jamar. In the morning I just feel like I really want to be his friend, but the fact that he’s dating my sister makes it awkward. I spoke to him briefly this morning when he and Lydia were eating breakfast and I asked for his number which he gave to me.

I just want to ask him if he wants to hang out with me some time (without Lydia) but I feel like things would be incredibly awkward between us if I did and he said no. Do other people become friends with their siblings’ partners? I feel like I’m just being a huge weirdo and I’m very anxious about making things awkward between me, Lydia and Jamar by trying too hard to be his friend, but I like him a lot. Should I start by just trying to converse with him later via text and see where it goes?

TL;DR! – I’m afraid it’ll be awkward with him if he doesn’t really want to be friends with me, or awkward with my sister if we do become good friends.

22 comments
  1. You could start with some small chatting on work or when he comed over!

    It’s not weird at all, actually it’s sweet

  2. Just ask him if he wants to hang out sometime. It’s normal to bond with your perhaps future “brother in law”

  3. Nah, it’s nice if you’re friends with your sister’s partner. If you want to be more subtle about it, just arrange to hang out with both of them at first, and eventually just invite him to something that your sister wouldn’t want to do.

  4. You’re being needlessly weird about this. I’m sure he wants to be liked by his gf’s brother. Invite him out tondo something fun that’s clearly a guys-only event and go have a good time.

  5. Just see if he wants to hang out and do something. Just remember that his priority is going to be your sister, and you need to be chill about that

  6. Why not just talk to your sister about it? I’m sure she would love for both of y’all to be pals and maybe all three of you could do something before you branch off and form a friendship with him since you feel awkward about it.

  7. I think you are seriously overthinking this. Unless you and your sister hate each other, generally speaking most people want their SO’s to get along with their siblings. If you are truly uncomfortable in this, ask your sister if she is okay with it for reassurance. I doubt she’d object to you being friends with him. She certainly didn’t object when you asked him for his phone number.

  8. Married lady here – my husband is good friends with my brothers. They hang out without me and game and stuff all the time. It’s honestly great. Hang out with Jamar! Having a friendly family unit is great

  9. It’s totally normal and good to be friends with siblings partners. Especially if they’re in it for the long haul, as that could be your future brother in law. Let the friendship grow naturally. Nothing to be weird or awkward about – unless you get into the jealous territory of who’s spending more time with who or if there’s a chance your feeling more than friendship for Jamar and possibly developing a crush.

  10. This sounds weird. Go make some friends elsewhere. It’ll really be weird when they breakup.

  11. My brother and husband are great friends. There is literally nothing better. The only thing that would make it awkward is if they break up

  12. Friendships build slowly. Build a friendship through spending the little bits of time together that you already spend, and go from there. Don’t put in a formal “can we be friends” application because that’s weird.

  13. Ask yourself if there’s a potential for you to develop feelings for him. Be honest with yourself.

  14. Small talk and food always a good way to start.

    Learn what you have in common and see where it goes.

  15. This isn’t strange at all. I’m actually closer now with my sister in law than I am with my brother

  16. I don’t know your orientation, but unless you have some sexual attraction to him, I think you are really overthinking this.

    If you guys hit it off as friends, I’m sure there will be more occasions for you to hang out. And, as other commenters suggested, you can invite him to do things that you do with your other guy friends.

  17. Nothing weird at all. It doesn’t get weird until they break up and put you in the middle.

  18. Why would it be awkward for your sister to date someone you are friends with? Not understanding this issue…

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