How can I tell my brother’s friend I like him?

[Anonymous]

I need serious advice please. We’re both adults, I’m 31 and he is 28. He’s my brother’s good friend. As of late I’ve been hanging out with my brother & the friend & I’ve caught feelings. I‘ve met him a bunch of times recently & every time I find myself thinking wow he’s such a nice guy. I can completely be myself around him & we have A LOT in common. The banter is amazing. I know he’s single too. However, I just don’t know if he sees me as anything other than his mates sister so I don’t know if he is just being nice to me because of that reason but my brother vouches he is a nice guy & my brother also knows I like him but thinks the guy should be the one to initiate first. My brother doesn’t want to make it awkward by trying to set us up but I feel like the friend is too reserved to initiate himself, he’s not a confident type of guy so I doubt hitting on me has even crossed his mind. He’s also not on social media so I can’t add him & I don’t have his number either grrrr! I’m just at the mercy of my brother & him making plans to meet & then tagging along with them.
Here is the interesting part - the guy asks my brother about me from time to time & tells him to bring me too when they meet up so that is all I have to believe that he may like me too.
Last time we met, my brother went to the toilet so it was just the two of us so I kind of made a move on him. We were talking about relationships & I casually said where can I find a guy like you? He gasped, smiled, looked away and basically got flustered and red in the face. I don’t know if he was blushing because he likes me or because I made him uncomfortable.

Does anyone have any sound advice on how to keep giving him hints? I just feel like good men like him are so FEW & FAR between & I genuinely see a connection with him. I have not had much luck in dating & I may always wonder WHAT IF with this guy, but if he doesn’t feel the same way I risk looking like the creepy sister & I may ruin my brothers friendship.

Updates

+1 y

At the end of the year he may also be moving away. This is something I only found out recently and it’s made me even more torn.. do I move quicker on him OR just let it all go and not take any action? If he’s going to move away, me confessing my feelings won’t make him stay, but we could do long distance at least, or if I confess and he doesn’t like me the fact that he’s moving will make it easier to get over it and I won’t have to see him again.

[PrettyPriya]

Here is the key and answer to your question "We’re both adults". Sorted. That is all you need to know. Just do what any adult would do and ask him to lunch or something. You know, it doesn't have to be the guy that asks the girl out. I asked my now husband on our first date.

I don't see anything negative going on here other than you are hesitant. You like the guy. You find that he has good character and personality that fit yours. Your brother vouches for him and approves. What is not to like about this situation. Unless I am misreading something, go for it.

If you find that you can not ask him to lunch or something like that, you are going to have to send out some signals by flirting. I already get the feeling you do that. Best bet is to take the plunge. As you put it, good guys are few and far between. You don't want to waste an opportunity, do you?

[Asker]

Yes I think you’re right. I really don’t want to waste this opportunity but at the same time I’m not very good at flirting either. Any tips?

[PrettyPriya]

For flirting or... like how flat out ask him out? I am good at both hahaha. 🙂

[Asker]

I’d like to hint a little more to him first so need tips for flirting haha but nothing too over the top because like I said I’m not good at it and he is also kinda shy so I don’t want to make him feel uncomfortable. Something that conveys my interest but doesn’t give off desperate vibes.

[PrettyPriya]

I know exactly what you mean. So, let me ask this. When do you see/talk to him most often? That will give me a better idea of how to kinda nudge him in the right direction. Context of when you two are around each other will be important.

[Asker]

So we usually meet around twice a month, the 3 of us, my brother included. Him and I have never met alone. We go grab a coffee or some food and are sat opposite each other always. There has been no physical touch except the last time I kind of gave him a side hug when saying goodbye. My brother sometimes gets up to smoke or use the toilet, but other than that he’s always present so makes it a bit hard to sneak the hints in. Because even if I don’t mind flirting in front of my brother, I’m sure the guy will feel awkward reciprocating if my brother is literally sat there too.

[PrettyPriya]

Oh boy. You aren't making it easy on me, are you? I'm trying to insert myself in this scenario. I do have an older brother so I can somewhat relate.

Okay, simple and easy. I am assuming you do not go for just one coffee, no? If it were me, I would do one of two things depending on how it played out.

If he goes up to get another coffee, you do too. Simples. Now, this gives you however brief a moment (s) to flirt a little. Smile, laugh, EYE CONTACT and even a playful grab of the (and this is important) elbow. Guys love that take charge feeling. Only has to be for a second if you laugh at something or "Oh, yeah I heard they are having that event blah blah blah too!" *grab elbow/arm for a moment.

How you have established just a bit of simple intimacy. Second scenario is a little tougher but not undoable. Everyone is sitting around. More coffee needed. Volunteer to go and ask ______ if he would be so kind to help you.

In this case, when you ask, smile and hold that eye contact. Again, after that and waiting for coffees, you can do same as the first.

Just an idea of what I would do. What do ya think?

[Asker]

Yeahhh I’ve been meaning to touch his arm but it just hasn’t happened as yet but I think I’m going to have to be a little strategic from now on! I’ll 100% take your advice because I’ve not got much of an idea of what else to do. Thank you for helping me out, I really appreciate it! :)

[PrettyPriya]

Oh most welcome! I think just getting yourself into that position where you can get a little playful and handsy is the toughest part. I gave an example. You can tailor it to the situation you are actually in as you see fit.

Point is that get yourself into a position that you can do that. Best of luck to you!! Have a great weekend. 🙂

[Asker]

Just one last question-when I asked him “where can I find a guy like you?” And he kind of looked shocked, gasped and blushed, was that more of a good sign or a bad one? He literally repeated and remarked “a guy like me?” I couldn’t decipher if his reaction was good or bad.

[PrettyPriya]

That is a good thing. I bet is was more of an unprepared type of a reaction. Imagine if someone said that to you out of the blue. I know I would have been taken aback a bit. Flattered but a bit stunned in the moment. Not a negative thing though.

[PrettyPriya]

Thank you for the MHO 🙂

[Asker]

Heyy! I wanted to come back here to update you. I met up with the guy yesterday, in a group setting we met after like a month, but it was really nice. I think we made progress because we got some alone time too. We met up with some friends in one cafe then we all drove to another restaurant. He didn’t know the way so I seized the opportunity and told him I did so I’ll just sit with him in the car and once I got in the car and it was just the two of us I joked and said I have a confession I don’t really know the way LOL I think he picked up on it because when we got to the restaurant things kinda got weird in a good way. There was a lot of banter and he teased me a lot. I even touched him on his arm but completely naturally I didn’t even realise I did it until I was touching him. And even though there was 3 other people there including my brother, the two of us kept talking to each other, to the point that one of the girls who we had met for the first time remarked to me later on that she thought him and I were a thing and when I gave the lowdown to her, she was like yeah it definitely seems like he likes you. My brother also remarked the guy was different and that there was a flirty vibe. Now in two weeks his bday is coming up. I want to wish him but I a till don’t have his phone number, though I plan on taking it from my brother and to send him a happy birthday text. Is there anyway I can send a slight flirty happy bday text? Or do I just keep it short and simple and then see if he carries on the conversation?

[PrettyPriya]

Oh wow! This all sounds like good, positive interactions!! I’m so happy for you.

Okay, so the text for the birthday. I would start with something simple and then if the conversation continues you could get flirty.

I like that your friend had the same opinion that I did about him liking you. That is just more (direct) validation that he does. I’m happy to help if I can!

[Asker]

Haha thank you for being so supportive! My friends in real life are kind of sick of me talking about him so it helps to have a strangers opinion! Do you think it’ll be toooo obvious if I wish him on his bday given the fact that we never exchanged numbers so if I text him he mayyy think oh wow she asked her brother for my number? Like even though it’ll be just a harmless birthday wish, the thought will cross his mind that I did actively seek out his number

[Asker]

And he isn’t on social media so I can’t wish him any other way, it’ll have to be via a text!

[PrettyPriya]

No!! I think it is totally appropriate wishing him happy birthday! Go for it!

Just do that, which is casual, and then see if you can continue conversation and see where it goes. Even by text, you should be able to pick up on things. I’m here if you need feedback.

[Asker]

Thanks! Will update in two weeks haha wish me luck!

[PrettyPriya]

Best of luck hun! Can’t wait to hear about how it went!!

[AviatorTom]

Notice to all Women... Guys are not good at taking hints, we guys prefer that you be blunt.

So, next time you're together, tell him you like him and ask him out on a date. It's not that hard.

[Guy13]

Go have a casual martini 🍸 🫒 snd talk like normal people do. It should be fun and maybe walk downtown some….

[Asker]

So can you tell me as a guy, when making a plan, what is the thought process on asking a friend to bring his sister along too? He’s asked my brother to bring me too almost every time they meet. Could he be interested in me or does he just like my company? Keep in mind no other guy friend of my brothers has ever said the same

[Guy13]

He can check you out with family. That’s the move of a thoughtful person but I have no idea of his intentions

[TrillXHippy]

*breathes in and out repeatedly* Just tell him

[Asker]

I could do that but past experience of being straight up with men has led to me getting rejected a lot. Apparently then it becomes t”too easy” men get the “ick”

[In_Trance]

Straight up