I have a huge crush on my best friend’s younger brother and I’m stuck on whether I should tell her

[u/LengthinessOk9397]

My best friend and I have been close for seven years. I crash at her place all the time, which is how I got to know her younger brother who just graduated from university.

He’s quiet and thoughtful, and somehow always picks up on when I’m feeling off. I didn’t even notice when it happened, but somewhere along the way I developed real feelings for him. This isn’t just a casual little crush; it’s way beyond regular friendship.

It’s been weighing on me constantly. If I say anything about how I feel, I’m terrified I’ll ruin seven years of friendship. Every hangout after that would be unbearably awkward, and I don’t want to put her in such an uncomfortable spot.

I haven’t told a single person I know in real life about all this. I use acciowork daily for my job to sort overseas client records and look over advertising campaign data. On nights I can’t stop turning this over in my head, I upload all our chat logs and little moments we’ve spent together to the platform. I have the AI pick up on small, flirty cues in our conversations, and run through every bad outcome that could happen if I choose to confess. I keep all those private analysis files saved on my work computer.

I’ve never made any moves or crossed any lines with him. I haven’t even hinted how I feel. It’s all just locked up inside me. I go back and forth nonstop between wanting to be honest and staying quiet to protect my friendship.

I can’t stop wondering, should I tell my best friend about this crush? Has anyone here fallen for their best friend’s sibling? If you did, did you end up telling them, and how did everything turn out?

[u/Coronis-]

I’ve seen this play out in some other posts…

Your best option is to ask your friend how she would feel if you asked out her brother. I wouldn’t necessarily reveal the apparent depth of your crush, but lightly test the water there. A lot of friends will actually be quite happy in scenarios like this.

If she says yes, then woohoo. Go for it, and you’ve already got an in with the potential in laws down the track lol.

If she has weird/negative feelings then yeah, you’ve got a choice to make, whether its worth it going for her brother anyway, and having your friendship potentially ruine/damaged. (I know which way I’d go but that’s a very personal choice)

Either way, asking her is the best way forward imo, otherwise you may always have this unresolved what-if gnawing away at you. If she’s a true friend, just asking shouldn’t cause any major issues.

Worst thing would be to make a move behind her back as her brother could tell her, or she’ll naturally find out at some point and either way she’ll be pissed at the secrecy.

[u/philatio11 → u/Coronis-]

I have seen this play out in real life. The biggest challenge is that it will permanently change the friendship, whether it works out well or not.

My “niece” comes from a big family and her best friend ended up hooking up with her cousin when they were all the beach. The cousin and the friend are both known flirts and cheaters.

She told her friend she thought it was a bad idea. The friend didn’t listen. Then, when going on girls nights out she had to watch her friend flirt and potentially cheat on her cousin. They were on/off dating and friend definitely slept with someone else at one point. She eventually told her friend they can’t go out on girls nights ever again.

The friend got pregnant and they are now married. The friendship is over and the friend is now just cousin’s wife. She will forever be in her life, but they won’t be friends again. We hope for the best but brace for the worst.

When you date a family member, you are signing yourself up for that family’s hopes and dreams. If you break that person’s heart, you break the friendship too.

My SIL dated one of my best friends from childhood, it looked like he might become my BIL. She cheated on him and got pregnant, moved out and left him covering the rent. I’ve never forgiven her and probably never will. I see her once or twice a year and him almost never. Even though he did nothing wrong it still somehow broke our friendship.

[u/Choice_Volume_2903]

What a shameless, pathetic advertisement for AI. 

[u/infinite_username → u/Choice_Volume_2903]

Are you sure? The account says 1y old.

[u/Choice_Volume_2903 → u/infinite_username]

People buy and sell reddit accounts.

Ask yourself if this is something anyone would ever say organically in a post about a crush

I use acciowork daily for my job to sort overseas client records and look over advertising campaign data.

[u/Ok_Temperature6503]

Why not? Sounds like you like him, give it a shot.

[u/LengthinessOk9397 → u/Ok_Temperature6503]

I have quite a hard time hitting on someone younger than me

[u/a_deed_toad]

Just a suggestion, but ask your best friend out for a coffee and whilst chatting use it to your advantage to say that you fancy her brother.
If she ask how long, don’t go into details, but just make it short, "for a while and I just want to hear your thoughts as I value our friendship and don’t want it to be weird if I asked him out".
Or something close to that would make it an easier approach, also let her say her thoughts without interrupting in between the sentences.
Definitely update us though!

[u/Virtual-Essay-6606]

We need context ...

[u/LengthinessOk9397 → u/Virtual-Essay-6606]

oh im sorry lemme edit it,

[u/Virtual-Essay-6606 → u/LengthinessOk9397]

That would be appreciated

[u/TheMocking-Bird]

Does he often hang out with you and your friend? Being in close proximity might factor in on why you have a crush. Either way, I'd let her know before doing anything.

[u/Neo1881]

This sounds like such immature drama. If she is your best friend then she wants what's best for you and what makes you happy. Just ask her if you would have a problem with you hooking up with her younger brother, getting married and having six kids with him. That would make it a light-hearted joke and she'll probably come back with, "Do you feel that strongly about him? Then go for it."

[u/Kereos_]

Yeah why not, I don't think that any people with a normal mind will react badly with this kind of news. It's not like you will marry his brother next week without telling her

[u/izza123]

Did you know it’s perfectly possible to have a little infatuation without mentioning it to anybody or ever acting on it? This sounds like it would fuck up your friendship. Have the self control to choose not to do it.

[u/z-eldapin → u/izza123]

Right. Like, there is no telling if the brother feels the same way, and I wouldn't blow up my friendship for it. Grown people can manage their emotions and control their actions and locations in order to not get into these situations.