My flatmate's sister...

[Fruit]

Hi there, I have a bit of a situation and I would like to get a neutral perspective on things.

I'm a 25 year old guy and I live with 2 other people, Liam and Sally. Liam and Sally are in a relationship, but I am good friends with both of them and have known them both at least a couple of years each. Although I'm the 3rd person in our flat, we get along greatly and we all enjoy living together, we get on really well. They are also both in their early/mid twenties.

Sally has a younger sister, Emma, who is 20. Liam and Sally both work full time but me and Emma both go to the same university, albeit different subjects. Of course, I met Emma through Sally. I don't know her as well as my flatmates but I get on well with her. Emma comes over to our flat regularly which is understandable considering her sister lives here.

Whenever I hang out with Emma, it would only ever usually include Liam and Sally as well, more like a group and maybe a couple of others, so I had never hung out with Emma without Liam and/or Sally.

A month or so ago, Emma messaged me and asked if I wanted to go out for drinks with her and her flatmates, who I hadn't met yet. She also asked my brother (who has met her a few times but knows her less) as well as Liam and Sally. I'm not much of a drinker/go outer, but I thought it could be fun. Neither my brother, Liam or Sally could make it, but I went.

The afternoon before that evening I was home alone in my bedroom working on an assignment when she walked into our flat. She told me she had come over to try on some of Sally's dresses etc for that night, I thought nothing of it. (Sisters lending each other their clothes etc seems pretty normal)

She got changed presumably in Sally's room but each time she tried a new dress on she would stand at my bedroom door and ask me how she looked. Asking me if I thought she looked sexy or if I could see her underwear through the dress, or how it made her boobs look, did it make her butt look good etc. Just really giving me ample opportunity to check her out. Honestly she looked very attractive, I told her she looked good. She was giving off a very flirtatious vibe. It might be worth noting that when she came over she knew Liam and Sally would still be at work but that I would probably be home.

That night she was actually sober driving, but between places and in places she would stick close to me and hold my arm, saying she needed help walking in her heels. It did come off as flirtatious and I never expected it from her, but she was close and touchy. I went along with it, I've always played it cool around her, sort of like I'll happily chat to you but I'd never go out of my way to see you kind of way.

Nothing else notable happened that night and for the next couple of weeks we only really spoke briefly on facebook or if she came over to our flat if I happened to be home.


A couple of weeks later and it is a friday evening, I am bored and none of my friends seem to be available. I send a snapchat to several people including Emma asking what to do tonight. Emma replies with

"Come and watch a movie with me haha"
"Hmm I could be keen"
"What kind of movie do you want to watch?"
"Anything that isn't a rom com"

Anyway, without deciding on what to watch I got to hers at 10pm. I messaged her when I was there and she came to the door to let me in. Did we go to the living room and watch something with the rest of her flatmates? Nope, she took me into her bedroom and told me to get comfortable on her bed. Emphasis on ON and not IN.

Now at this point I'm really really wondering what to think. She even has the mood lighting thing going with only a lamp and a candle providing any light. We chatted for a bit and had a brief catch up as we decided on a movie, she invited me to get under her blanket with her (still not in the bed but on it under a blanket, it was cold).

During the movie, I was lying on my back and she was lying on her side, facing me and close enough that our arms/legs were touching. She made a few hints such as (referring to someone in the movie)
"Terry isn't really the kind of name I'd like to be saying during sex"
"Do you prefer a shorter name?"
Yeah I think so"
"Fruit is only one syllable"
"Oh yeah it is"

We saw the movie out, nothing happened. One key fact is I did NOT make a move on her. After the movie had finished we chatted quite a bit more, and at one point she asked me if Sally knew if I was there at her house. I hadn't told her I was going to hang out with her sister at her house, so no Sally had no idea. To which Emma replied "It's not like we had sex though". She also seemed to bring up sex a lot at many points...I left at around 2am.

Since then the exam period has hit and we haven't seen each other much or spoken too much.


Now, my question is, is Emma in to me?


From my point of view it is very risky as she is the sister of my flatmate who I am good friends with. Although I know Sally thinks highly of me, especially when it comes to girls, I still feel it isn't worth it. I asked my brother what he thought and he said he thought it was obvious that Emma was in to me, but I have a bit of a record for being oblivious. What do you think?

Thanks so much for reading, sorry it's so long!

[TheEvilJester]

Man, you sound so much like me. LOL! I'm as oblivious/uncertain as you. In fact, I may even have you beat, honestly. If it were me in exactly the situation you describe, not only would I be uncertain if she was into me, I'd probably be 100% convinced there is no way she could be, so I wouldn't even bother to entertain the thought. So, I'm so frigging jealous of you right now. LOL!

Being on the outside and hearing the story you tell.... yeah, it sounds pretty clear she probably is into you. Don't get me wrong. There are no guarantees. Some people are just more open and flirty by nature, so there is that possibility. Still, it sounds pretty likely she is into you, so if you want to, it is at least worth asking her out.

Now, there is the possible awkwardness of her being your friend/roomie's sister. I suppose if it makes you feel better you could maybe talk to your roomie about it first. Just something like "Hey, I kinda think I'd like to ask your sister out. Her and I really seem to get along. But, I didn't want to do it without at least talking to you first."

I mean, in the grand scheme of things, if you feel like your friendship with your roomie is too important to risk the possibility that A) she won't like it or B) it would be awkward if it doesn't go well between her and your sister, then maybe your decision is not to bother. However, if you like this gal, and it seems she might like you, why would you allow yourself to miss out on the opportunity to see if there could be something there? Nothing ventured, nothing gained, my friend.

Heck, do it for me. Nothing like this is ever going to happen to me, so I want to live vicariously through you. LOL! I'm kidding, of course. Do this for you, not some random evil stranger on the interwebs. I get why you have some doubts about it, but it isn't like it is your best friend's ex or something like that. So, at least in my opinion, there isn't any taboo about this. You are two adults who have every right to date if you want. Good luck to you. Whatever you decide, I hope it goes well.

[melancholia]

It sounds like she is into you for sure, because while some people are naturally flirtatious in nature, you two have spent some one on one time together, and she seems to be giving you some pretty clear signs that she's into you. Maybe she's nervous to make the first move as well.

While there may be some hesitation to start something up with your flatmate's sibling, you two are both adults and are free to choose to date whomever you want. It shouldn't bother her sister, especially if you and Sally are friends.

I understand that it could get tricky if things don't work out between you and Emma, but at least you live with her sister and not her... that would be a disaster for sure. As long as you are respectful of Emma, I don't see how Sally could take issue with that. Although I do know some insane people who say their siblings are off limits to their friends, but those people are overly controlling and very close-minded. I think if you and Emma continue to hang out together, and if you two decide to start dating, then you can bring it up to Sally and see what she thinks. Try not to go into it with an idea in your mind of what other people may think about it. Sally may like the idea of you two being together, or she may not; but it's not up to her to decide that, it's up to you and Emma.

I think you should ask Emma out on a date. See what happens from there; and don't forget to enjoy yourself and have fun!

[bloodtippedrose]

^ These guys said it all, just wanted to also confirm that I believe she is very into you! She flirts like I do, hardcore but still waits for the guy to make the move.

I dated my best friends (almost brother-like) cousin before, it was quite awkward around her and she was very uncomfortable and spiteful at first but she got over it.

[TheEvilJester]

Exactly. Even if, for any reason, your roomie does find it weird or is uncomfortable with it... if things progress between you two, eventually she'd come to accept it. Heck, if she's your friend, why wouldn't she want somebody like you to wind up with her sister? So, I do think you are a good fella for worrying about your friend/roomie's feeling in this, but you shouldn't let that stop you from pursuing possible love. It would be one thing if your intention was just to "hook up" with her sister, but if your intentions are perfectly noble (i.e. you hope to have a relationship, not just a fling) then I don't think you should let what anybody thinks stop you from possibly finding a good relationship.

[melancholia]

I think more often than not, people are excited for their friends to date their siblings. Clearly, when you are friends with someone, you care about them and see their good qualities. It's only natural to want someone you like and trust to date your sibling, whom you hope will find someone who loves, respects, and cares for them. If you and Sally are good friends, then I don't see why she would take issue with you fancying her sister.

[TheEvilJester]

I think more often than not, people are excited for their friends to date their siblings. Clearly, when you are friends with someone, you care about them and see their good qualities.

True. Exactly. Well, that is except for those situations where you are friends with somebody/enjoy their company because they are the delightful F up of the group. Like, they are a complete idiot and/or a scumbag, but in a fun/lovable kind of way. Good to have as a friend.... but not somebody you'd want to date, nor somebody you'd want to allow to date somebody for whom you care. LOL!

So, yeah, if you are the group's lovable d-bag, maybe she'd have a problem with you dating her sister. LOL! I don't get the impression you are the lovable d-bag, though. I mean, I could be wrong, but you sound like a good bloke. So, as we've said, why let what other people might think keep you from pursuing something that could possibly make you very happy?