My best friend's brother of all people!

[Rocker-Chick]

I’m a 24 year old woman and I’ve been single for about six months now after breaking up with my boyfriend of four years back in March. I’m currently working as a medical receptionist at an optometrist’s office. That will play into this.

My best friend and I have known each other since third grade. We’re basically sisters at this point. She and I have stuck together through all these years. She’s also got an older brother who is two years older than us. He always pretty much ignored me as kids. When we were teenagers we’d say hi to each other at school but we were never particularly close. After high school he joined the navy and I didn’t see him for a long time.

Fast forward to last month and her brother who I haven’t seen in years suddenly walks into my life. He is now working as a mail carrier and one day last month he came into our office to drop off the mail. I didn’t recognize him at first because he had grown a beard and slimmed down some. 

But he recognized me immediately. He smiled said hi and we started to talk. Right away I felt like this conversation was way different than our old small talk back in the day. It seemed like he was being flirtatious with me but I thought it might be my imagination.

But it wasn’t. We’ve been flirting really hard for the last few weeks every time he comes into the office to deliver. It’s gotten so obvious that even one of my bosses commented on it and he’s usually pretty oblivious as to what goes on up front.

I mentioned to my friend that her brother was delivering our mail now and she said he’d told her he saw me from time to time. It seems like he didn’t mention to her that we’ve been really flirting a lot or that he was interested in me.

This Monday when he came in he dropped the hint that while he was going to be working this whole week, he’d be off all next weekend. He said he didn’t have any real plans for his weekend off and was trying to figure out what to do. I told him if he thought of something good to let me know since I was free all of next weekend myself. 

This morning he came in and said he’d heard of a pretty good taco and tequila bar and asked if I’d like to try it out with him. I said I’d love to. Then I asked if he’d talked to his sister at all about me. He said he hadn’t really. 

But I think I owe it to my best friend to tell her that I’m going to go on a date with her brother. I know the both of us have called it “just hanging out” but it’s definitely a date. There’s a real spark with him that I haven’t felt in a long time. I’m kind of nervous to bring this up to her. We’ve never really discussed dating each other’s siblings so I don’t know how she’s going to feel about this. 
 

 

[Gaeta]

I think you're worrying for nothing. Let her know her brother invited you out to this place and don't make it sound like  a big deal. At this point you don't even know if there will be a 2nd date.

By the way l married my best friend's brother. I was not familiar with him as he was away in the army. We met, hit it off, my friend was thrilled about it.  

[Nothanks]

You should let her know about the date.  You may need some boundaries on what you decide to share with her.    If you historically have shared every detail about your dates with her, you may not want to do that in this case.  She probably doesn’t want to hear intimate details about her brother’s dating behaviour or negative comments if things don’t  go well.  I’d keep things high level and as positive as possible.  Good luck!

[Wiseman2]

She'll eventually find out and what's the big deal about her knowing anyway?

You and her brother are your own people and adults. You don't need anyone's blessings.

Have fun on the date.

[Rocker-Chick]

44 minutes ago, Wiseman2 said:

She'll eventually find out and what's the big deal about her knowing anyway?

You and her brother are your own people and adults. You don't need anyone's blessings.

Have fun on the date.

Thanks! I want her to know that I’m not using her brother as a rebound. I’m genuinely interested in him and seeing where this goes.  From our little chats he seems like a really sweet and funny guy. Plus she’s been my best friend for my whole life, my sister for all intents and purposes. She’s the first person I’d tell about a date with any guy. Her brother is a little bit different than any other guy though. I know we don’t need her blessing per se, but I’d like to make sure she’s ok with us seeing each other.

[glows]

Go with your gut feeling on this and mention this if you only feel it's necessary. I think worrying about her thinking he's a rebound for you is peculiar or you seem low on confidence in yourself. Why would she think that? Wouldn't she have more faith in you or does she think you're irresponsible or reckless with others' feelings? You may be overthinking in that aspect. 

[Wiseman2]

39 minutes ago, Rocker-Chick said:

 I’d like to make sure she’s ok with us seeing each other.

But you are already planning a date, so? Don't worry about it. Her brother is a big boy and calls his own shots.

He's not going to rearrange who he wants to date according to what his kid sister thinks.

If you think it could get awkward or adversely affect your friendship. Stop flirting and cancel the date.

[Blind-Sided]

as @Gaeta said... you are worrying about nothing.  You are adults, and the reason you friend may not know yet is... her and her brother may not talk that much.  It's not like they are kids, living at home.  My brother and I would do anything for each other... but I may not talk to him for weeks on end.   And because of the way we communicate... I wouldn't tell him about a girl  until I knew something was real.

Go out, and see how it goes.  If it leads to another date... then worry about your friend.  BUT... if she is your friend... she will be happy for you both.

[Rocker-Chick]

6 hours ago, glows said:

Go with your gut feeling on this and mention this if you only feel it's necessary. I think worrying about her thinking he's a rebound for you is peculiar or you seem low on confidence in yourself. Why would she think that? Wouldn't she have more faith in you or does she think you're irresponsible or reckless with others' feelings? You may be overthinking in that aspect. 

You are probably correct. I’m probably overthinking this whole situation. I haven’t been on a first date in so long that I’m imagining problems that probably don’t even exist. In any case I’m having lunch with my friend this afternoon and I’m going to tell her about me and her brother. 
 

 

[Rocker-Chick]

3 hours ago, Blind-Sided said:

as @Gaeta said... you are worrying about nothing.  You are adults, and the reason you friend may not know yet is... her and her brother may not talk that much.  It's not like they are kids, living at home.  My brother and I would do anything for each other... but I may not talk to him for weeks on end.   And because of the way we communicate... I wouldn't tell him about a girl  until I knew something was real.

Go out, and see how it goes.  If it leads to another date... then worry about your friend.  BUT... if she is your friend... she will be happy for you both.

Thanks. I’m probably overthinking the whole thing. I’m somewhat of a worrier by nature. This really good thing that had seemingly fallen into my lap should make me happy but my neurotic nature of course has me worried something could mess it up.

But I’m also so excited for our date in Saturday! He seems so nice and genuinely interested in me and I can’t wait to get to know him better.

[glows]

8 minutes ago, Rocker-Chick said:

You are probably correct. I’m probably overthinking this whole situation. I haven’t been on a first date in so long that I’m imagining problems that probably don’t even exist. In any case I’m having lunch with my friend this afternoon and I’m going to tell her about me and her brother. 
 

 

The reasons I would avoid telling anyone this earlier as in now, today, is 1) it's no one's business and having food/drinks at a taco and tequila bar doesn't constitute a date (both of you are just scoping each other out and going out for a good time) and 2) I prefer checking someone out independently without added comments from, let's say, a sibling or sister. If you both hit it off and start dating four or five dates down the line then I might say something then. 

Maybe go over the reasons for letting her know this early. If it's a courtesy thing, I wouldn't tell her this early.

 

[smackie9]

There's a reason why he hasn't mentioned much to his sister....he doesn't want her involved in his business. If the date goes well, maybe mention it to him first, and see how he feels about letting her know.

[GeorgiaPeach1]

I personally would not flirt with my best friend's brother behind her back, nor would I date him. There are billions of other men on the planet. This is going to mess your friendship up big time, as she will be put in a very uncomfortable position when you and her brother have dating/relationship issues. 

[elaine567]

If this girl is like a sister to you and your relationship is such you tell each other everything, she is not going to be best pleased that you and her brother are sneaking around behind her back.
 

[stillafool]

8 minutes ago, GeorgiaPeach1 said:

I personally would not flirt with my best friend's brother behind her back, nor would I date him. There are billions of other men on the planet. This is going to mess your friendship up big time, as she will be put in a very uncomfortable position when you and her brother have dating/relationship issues. 

I'm the same way.  My best friend's brother asked me out and even though it killed me because he was drop dead good looking, I declined.  There are too many men out there to risk losing my best friend.

[Rocker-Chick]

53 minutes ago, elaine567 said:

If this girl is like a sister to you and your relationship is such you tell each other everything, she is not going to be best pleased that you and her brother are sneaking around behind her back.
 

Are we sneaking? We’ve been flirting, sure. We made a date and I’m going to tell her before the date even happens about it.

[Wiseman2]

1 minute ago, Rocker-Chick said:

Are we sneaking? 

Of course you're not. It's his sister not his GF. Relax. 

[Rocker-Chick]

2 minutes ago, Wiseman2 said:

Of course you're not. It's his sister not his GF. Relax. 

Of course. I was just responding to someone else who said we were sneaking.

[stillafool]

45 minutes ago, Rocker-Chick said:

Are we sneaking? We’ve been flirting, sure. We made a date and I’m going to tell her before the date even happens about it.

You should also let her know it was your suggestion but he came up with the plans.  If things go south between you and him don't complain about him to her.  That won't go well.

[ShyViolet]

You are all adults... you don't need her permission to go on a date with this man.  Do whatever you want.  But I definitely think you should mention it to her up front.  Be completely open and honest about it from the start, don't "hide" it from her, because then she's much more likely to feel weird about it.

[Rocker-Chick]

Hi everyone who commented. I just wanted to give a short update. I had lunch with my friend this afternoon and we talked about her brother. Her only advice to me was you only live once so why not go on a date and see what happens. She also said that either of us would be crazy to say no to a date with the other.

So that’s where it stands right now. We’re going to have dinner next Saturday and see if this flirtatious little thing we have going leads anywhere. Right now it’s just one date but I’m hoping for more.

[Wiseman2]

3 hours ago, Rocker-Chick said:

We’re going to have dinner next Saturday and see if this flirtatious little thing we have going leads anywhere. Right now it’s just one date but I’m hoping for more.

Excellent. Have fun.

[Rocker-Chick]

7 hours ago, GeorgiaPeach1 said:

I personally would not flirt with my best friend's brother behind her back, nor would I date him. There are billions of other men on the planet. This is going to mess your friendship up big time, as she will be put in a very uncomfortable position when you and her brother have dating/relationship issues. 

Maybe, maybe not. Yes there are billions of other guys on the planet but none of them are him. There’s something about him. If I didn’t think he was worth it I wouldn’t go out with him.

[stillafool]

1 hour ago, Rocker-Chick said:

as she will be put in a very uncomfortable position when you and her brother have dating/relationship issues. 

To negate this, if you do end up having issues don't talk to her about them.  Blood is always thickier than water.