Last summer I moved in with two randoms in a small town with terrible housing. One guy, one girl. When I found the place online, I was nervous about living with a guy bc I thought it might be awkward. What if I wanna bring someone home? What if he hears my loud stinky poops? What if he’s messy and a pig? Etc etc. I then toured the place and met the both of them and decided the place was too nice and too cheap to pass up. The girl was really sweet and we got along really well and he came off as a nerdy type so I thought I wouldn’t be into him and we could coexist.

I was wrong. The girl turned into a nightmare roommate. Super messy, very loud and inconsiderate. Fighting with her boyfriend, slamming doors and yelling in the middle of a night on a weeknight, blasting the TV at all hours. She also has two cats and the other roomate, let’s call him Tim, and I end up feeding them 70% of the time because she’ll be over at her boyfriends or with her friends.

Tim and I started off as friends and we were always friendly and positive, but after one particularly bad fight with the boyfriend, Tim and I started to talk about how much we didn’t like our other roomate. Realizing we were on the same page, we talked for hours and laughed for hours about stupid shit she did. We made little inside jokes and even a bingo board for the crap she pulls.

Over time we started talking more and more and now I think I’m in love with him. He’s my best friend. I trust him and feel so safe and comfortable around him. He’s so funny and kind, smart and artistic, he’s just such a well rounded person. When he plays guitar at night I literally melt. I have to go into another room or it’ll be so obvious how in love with him I am. I’ve told him all about my life and he’s told me about his. I really care about him and from what I can tell he at least seems to like me as a friend as well.

Here’s the thing. We’ve talked about our past relationships and he told me about this one relationship he had where he hooked up with a roomate and she turned out to be super manipulative and narcissistic. And he doesn’t use those words lightly. Things ended badly with her while they still lived together so he’s pretty scarred from that.

He also has gone on a date semi recently which makes me think he’s not interested in me. But I also dated someone for three months in the fall, but the whole time I was dating this other guy I was just thinking about him instead. It’s made it hard for me to want to see other people and I haven’t seen anyone since.

Friends have made comments about us hanging out a lot. We cook for eachother and watch movies together. We can have whole conversations in just a glance. I know this type of connection is rare. His brother came down two weekends ago and the three of us went to a concert together and played Mario kart after, and while Tim and I were jokingly trash talking, his brother said “ooo seems like there’s tension here” and then it got real quiet lol.

My question is, do I confess feelings or not? If yes, when? We have 3 months left on the lease. Considering our other batshit roomate and his bad past experiences, I think maybe not, but is that letting the moment pass? It’s getting to the point where it’s hard to be around him and hide it.

Also, my parents house is sitting empty 20 mins away, so I could offer to move back there to give him space either way. Honestly I might do that anyway bc of how bad the other roomate is. Another factor is that I might move 3 hours away after our lease is up. He knows this as well.

I just need your help! Do I confess at the end of the lease? Now? How do I go about it? I don’t want to make him feel uncomfortable here since he’s only lived in shitty situations and we already have our shitty other roomate. But now that I think about it, I don’t want to walk away from this having said nothing, it’s too special of a connection to do nothing. I know I can’t live with him again but I also know I’ll miss him when I move out.

What would you do if you were me?

TLDR: In love with my male roommate, and our other female roommate is terrible. He’s hooked up with a dif roomie in the past and it went very badly. 3 months left on the lease. What do I do?


40 comments

  1. honestly you should just tell him, life is too short for this shit. yeah he had bad experience before but that was with someone else who was manipulative – you’re not her

    maybe wait until you’re both away from the house so there’s no weird energy at home if things get awkward? like grab coffee somewhere neutral. and definitely mention the thing about your parents place so he knows you’re not trying to trap him in awkward living situation

    the timing sucks with only 3 months left but you’ll regret it forever if you don’t try

  3. I think you each are at a perfect age for this to work.

    Do you ever go out to eat, or to a concert, or just to walk and get coffee? Not exactly as a date, but as friends?

  4. You miss 100 % of the shots you don’t take – Some athlete.

    True connections don’t come by often.

  5. There’s a real possibility he has feelings for you too and has the same fears as well. You should just tell him how you feel now.

  6. I would just go for it and tell him. Might even be an advantage that your lease is up soon because then worse case if it doesn’t go well it’s just a couple awkward months and you move out. I’d say odds are in your favour though if he’s not actively seeing anyone and you hang out as much as you say you do. 

  8. Dating someone else doesn’t mean one’s not interested in someone else in my opinion, since it doesnt end up towards a relationship most of the time.
    You really seem in love with him seeing the way you talk about him and your relationship, so I’d say go for it !
    But move out. Both because of his past relationship, and because I think it is best to not live with eachother at the start of a relationship, for a lot of reasons.

  9. Yes, you absolutely do. I don’t even know if I’d wait. What if he finds someone by that time?
    You have nothing to loose. He says yes – great. He says no – he might still change his mind in the three months to come. Tell him you understand his past and you’re happy to take things slow. But if the guy talks with you for hours, you go out hanging together and you even met his brother, I think there’s a strong case his into you as well. I wouldn’t maybe use strong words like “love” if you haven’t even started dating yet, that might scare him off. Besides that, you should totally go for it, tell him you’re quite into him and would like to go out on a date if he’s up for it.

    Best of luck!

  10. unrelated but you sound like a really sweet and fun person. just from your responses and how you write, you seem very well rounded yourself! also reflected, you’ve thought of many aspects of the situation. good for you☺️

  12. Just ask if he’d be interested in going on a date, don’t hint or second guess anything. I’d he says yes, great (he will). If he says no, say ok all good and go on with what you were doing and hopefully it’s only awkward for 10 minutes.

  13. Gonna need an update on this.

    Absolutely tell him. These feelings shouldn’t be held in, and if you don’t you’ll always wonder. If you’re both mature the worst case scenario is it doesn’t work out and you have an amazing friend, but honestly, this sounds very cute. Good luck!

  14. Omg yes lol. I kept waiting for the other shoe to drop where there’s some big issue and there really wasn’t one. You guys are at a good age where “maybe you’ll move 3 hours away” isn’t an issue at all. You’re young enough to be free in your life choices but old enough to be able to handle a small distance like that if you had to. I wouldn’t even concern myself over that unless one of you is like deadset on only living in one place for the rest of your lives. You sound so adorable honestly and I hope you update us 🙂

  16. Listen — you just said you like him, the connection is rare, and you have an out relatively soon. Shoot your shot.

  17. Man, you guys are already doing the stuff couples do other than being intimate. I think he might have feelings for you too. You guys already live together so you don’t have to wonder what living with him feels like. I think you shoud just take the first move and tell him how you feel when you two get get a quiet moment to yourself next. Slow burn romances are always the best kind imo.

  20. Yes. Just confess. Jist do it because your lease ends anyway so if ir doesnt work out. Youre not trapped. But i had this once and after all these years regret never saying anything as i never found that again.

  21. Feelings are not a crime that you “confess.” Either make a move physically or ask him on a date.

  22. >What would you do if you were me?

    I’d go for it. I have so many missed opportunities looking back at my life. The saying is true, you miss 100% of the shots you don’t take.

    As for his previous experience, don’t let that determine your life experience. If he’s not interested he’ll let you know, then you be an adult and don’t let it affect roommate situation.

  23. Pretty clear people think it’s okay for you to go for it. Although I recommend the asking on a date approach rather than “confessing”. Confessing could be a bit intense or pressure inducing for him to “respond” right away. The asking on a date implies your interest and if he’s super into it, you both have the flexibility to share feelings over time.

  24. I say this every time someone posts something like this:

    You only get so many chances at finding true love. Don’t pass it up. Lay it all out there and worry about the consequences later.

  27. My roommate and I confessed to having feelings for each other 13 years ago. She’s still my roommate, the best I’ve ever had. But now we share a bed and she wears the wedding ring I bought for her.

  30. I think you’re putting too much weight on his past relationship. I mean sure it was horrible he did say as much, but he would have to be blind to not see that you’re completely different and I don’t have a single doubt in my mind that he knows this. He too feels the connection, though he might be better at hiding it then you. I say go for it. The worst that can happen is he’ll say no, or not right now, but I don’t think it will completely ruin what you guys have because the bond sounds really strong.

    Waiting till the end will be a bad idea since you guys might end up long distance because there wasn’t enough time to plan things out. I mean you’ve already skipped a *major* step by living with each other for this long and not hating each other so I’d say this is a match made in haven! Wishing you the best of luck, and update us will ya?

  31. Ugh I’ve been in this type of situation before and its a rough one. I hope the best for you! When I confessed how much I cared about him it wasnt mutual,(or so I thought) but we cared enough about eachother as friends that we still talk to this day! And then he confessed to me a couple years later that he wished he would’ve thought about it more because he said he hasnt met a girl like me still! 💔

  32. DO IT. I married my roommate. No regrets!

    Wasn’t planning to confess my crush until one of my friends started hitting on him at a party. I was drunk and livid and said too much. It worked out!

  33. I was in a similar situation. The lease was up in a few months. I was planning to stay local. She was moving a few states away.

    She was the one who made the first move. I’m so dense, I thought I was the only one who had feelings. I didn’t think I wanted to go to the next level because parting sucks when there are feelings.
    She was right though.

    We were on the down-low with regard to the other roommates for those few months.

    We both stayed local. We became more than roommates. It worked for three years until it no longer worked.

    Still, I’m happy for the three years we had together.

    Do it.

  34. Holy shit girl just tell him, just because he’s gone on a date recently doesn’t mean he’s not into you, it just means he may not realise you’re an option. As a guy, we can be stupidly oblivious.

    Otherwise you’ll spend the rest of your time going what if.

  35. Same thing happened to me. We’ve been happily married for 12 years. I was the one to break the ice. I told him before we even started dating that he was gonna marry me someday.

  36. I would confess now so that if it did work out, you have 3 months to set up your parents house and start saving for a down payment on you two’s own. The reason being, if it does work out, sounds like this is the one you’ve been waiting on.

  39. So idk why this set off a scenario in my head but this is how I imagine this goes down:

    He’s playing his guitar at night like he usually does. You hear him play for a little bit, before walking into his room and leaning on the door frame.

    “Where did you learn to play?” Or some other bullshit cause you already probably know that. Anything relating to his guitar playing.

    He starts telling you about that bullshit.

    You walk over and sit next to him.

    “Here let me try, can you show me how to play?”

    Snatch up that guitar from that boy. Sit right up next to him on the bed with the neck of the guitar in front of him. Now that you have the guitar he’s exposed like a scared animal with nothing physically separating you two. He may start to sweat.

    You start to play terribly because you don’t know how to play the fuckin guitar. Don’t full hog it, just a few shitty notes.

    Now you probably have to directly ask for this cause men are dumb and don’t pick up signals well, but you ask him to show you by putting his arms around you so he can hold your hands with his and move with you to play the guitar.

    ~Electricity~ shoots through your fingers and hands cause you fuckin like this boy. He feels it too. You can feel his heart beating through his chest.

    You slowly start to play the song he was playing before with him. You have a ~moment~ then song’s over.

    If he’s smart he slowly takes the guitar from you and puts that bullshit somewhere not on the bed. He turns to you, you look back. He puts his hand on your face, and leans in for the kiss.

    You kiss back.

    Congrats, you have acquired boyfriend. 👍

  40. Weird question, but are you guys close to the same level of attractiveness?

    I had a female roommate once that I was very close with. I honestly thought we were just good friends, as I wasn’t really physically attracted to her.

    One time when my other roommate and her were having a couple drinks, I started talking about this pretty girl that I met, and how we’re going on a date. She randomly started sobbing. She said she was fine and then she just might’ve had too many drinks. Her friend later told me that she was in love with me, that’s why she cried. I felt awful, and it was mildly awkward after that

    I would honestly wait until the lease is up before you say anything. Unless you’re getting clear signals.

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