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Best Friend's Sister


kkissinger

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So I'd like to get some unbiased opinions on the following scenario, especially regarding whether this is something I can actually consider: 
• I am a 29 year old male.
• I have been best friends with someone since college, but I met his younger sister (4 years younger than me) five years ago. 
• We hit it off when I was visiting my friend to the point that we ended up video chatting a ton (we live in different states), maybe twice a week, for months. Apparently after my visit, my friend's girlfriend (and now wife) mentioned to my friend's sister that she was overly friendly with me. 
• We slowed down on video chatting over the years, but we have continued texting nearly every day over the last five years, with only rare breaks, even through both of us dating other people (though that's one topic we've almost completely avoided with each other). She would also send me baked goods every few months. 
• We saw each other a few other times over the years, always when I was hanging out with my friend. At my friend's wedding, I had multiple people who didn't know me ask if we were dating, and we spent a good deal of time together including dancing. 
• Two years ago, I asked her how she felt about me, but she said she thought of me as a brother, so I told her I would continue to be her friend (and have done so). 
• In the past few months, we've stepped up how much we talk again as she prepared to move to a different state and out of her parents' home. She recently invited me to fly out and stay at her apartment once I'm vaccinated. She also asked if I would send her a small potted plant of my choosing as an apartment-warming gift (less than $5, so not like she's using me). She also wants to start doing video chats again, and she's been sending flirty (non-sexual) snapchats when she rarely sent actual pictures of herself before). 

So...am I being led on by someone who may just be naturally flirty, or is there potentially something to this? Thanks 

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She likes the ego boost that you have a crush on her. She told you she thinks of you like a brother, so believe her. Those types of friendships when young are common, but when one of you gets into a serious relationship, the old friendship/crush that involved flirtation either will, or should end.

Keeping this up will prevent you from bonding with a local, potential gf. And a potential gf will see you as a player and run far and fast when she finds out you're in communication with someone you've been crushing on for 5 years. Plus, if you moved by your friend and started dating, she'd think it's fine to text flirty snapchats to another guy who's crushing on her. Is that okay with you? She doesn't have a boundary in that area.

It's a merry-go-round that's going absolutely nowhere. Get off the ride and go explore. There are plenty of local fun, pretty women around who you can actually spend time with in 3D. 

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2 hours ago, kkissinger said:

Two years ago, I asked her how she felt about me, but she said she thought of me as a brother, so I told her I would continue to be her friend

This, is all you need to remember.

Stop looking further into it.

Because, IF anything were to happen,it would have long ago... BUT, way too many issue's

-She is so far away

- She is your buddies sister

- She is early 20's ?  You are almost 30.

 

As mentioned above, get your own life in gear now & look into dating gals much closer to you.

You have a friend with this young lady- appreciate & leave it at that. ( you wouldn't want a mess of this).

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I think the only way you’re going to know is if you’re direct with her. She’s invited you to come stay with her, you could use that as an opening to ask her if she’d be interested in trying a dinner date.

I realize she’s told you once that she sees you as a brother...but as time passes, people grow and change. Relationships also grow and change. You just have to find out if she’s open to that sort of change in your relationship. She may not ever see you that way, but there’s always a chance that she could. And you have to be honest with yourself about how you might handle the situation if she isn’t on board.

I married my brother’s best friend. Much crazier things have happened.

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Ask her straight out if her feelings have changed about you.  You chat frequently so it should be easy.  If she asks why just tell her you don't want any misunderstandings between you two.

 If this doesn't turn romantic this time around you need to cut this off.  It isn't healthy for you feeding that glimmer of hope you always carry.

Sack up and ask her, there is no other way to know.

Lost

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6 hours ago, kkissinger said:

 both of us dating other people.

, I asked her how she felt about me, but she said she thought of me as a brother, 

No one is leading you on. She's tried to step away. 

Have either of you been happy in long term relationships?

It's doubtful this one told that one to tell her to back off. She wants to back off. But. Without offending you because you're her brother's friend.

She sends cookies. Ok, like a family member might.

Unfortunately this description has a ring of unrequited love in it and looking for "signs" despite the clear-cut brother answer when you straight up asked her.

Stay friends if you want but as long as you're avoiding real and local relationships by holding a torch, be aware that this may lead to heartaches when she inevitably gets serious with someone.

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2 hours ago, lostandhurt said:

Ask her straight out if her feelings have changed about you.  You chat frequently so it should be easy.  If she asks why just tell her you don't want any misunderstandings between you two.

 If this doesn't turn romantic this time around you need to cut this off. 

Yes, agreed with all of the above. 

It would be a total waste of time and money (not to mention the health risk) to fly to see her if she doesn't have romantic feelings for you. 

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16 minutes ago, Wiseman2 said:

She doesn't. When he asked, her response was "she thought of him as a brother". Furthermore, they're both dating others.

He asked her two years ago. Things can change. 

Also, I interpreted OP's post as they continued talking even while they were dating others, but not necessarily that they are both currently in relationships. 

OP, can you clarify? Are either of you in relationships with other people at present? 

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8 hours ago, kkissinger said:

  invited me to fly out 

Do you want a LDR? What's wrong with the people you're dating locally?

Does she specifically state that she's interested in having a LDR will you or that the nebulous invite is for sex?

If not, asking her... again...if she wants you as a BF could backfire and get quite awkward for you, her and your friend (her brother).

With all the women in your area and age group why go after someone who "sees you as a brother"?

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Maybe she felt it was too awkward because of age difference way back and being brother's friend, plus the distance, and her living with her parents, etc. You still have some time to explore the possibility before vaccinations and travel opens up.

 

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Neither of us are in relationships. She is 25, I'm 29, so it's not a crazy age gap. I do recognize I'm probably grasping at straws, but I thought it was best to get some opinions. There isn't anything wrong with the people local other than that I just haven't found the right one yet. 

 

And thank you all for your responses to date.

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12 hours ago, kkissinger said:

. I do recognize I'm probably grasping at straws, 

Agree. You're grasping at straws. Don't go after a friend's kid sister. You'll just have to get more involved dating locally.

It seems you are lonely. That's not a good reason to pursue this.

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No not a big age gap now, but 20 to 24 is, in terms of maturity, and where you are at with life goals/priorities. The gap narrows at 25, when you stop growing, developing, etc. Maybe not for everyone, but for most.

TBH you are both adults, you do whatever you want. She's moving onto her next chapter in her life...independence!

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She sees you as a friend, and your friend telling you that you are getting too friendly may be a sign that your friend is not okay with you dating his sister.

I would start to set boundaries -- don't be so available to chat with her all the time. Don't be the male girlfriend. you are too accessible for her to express interest if there is any.  I would say that you will be happy to send her a plant, but you think it wouldn't be a good idea to stay at her place. You don't think her brother would approve of that/you don't sleep over with female friends.  You would be happy to meet up with her while you are in town next.

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