How to Ask Him to Be Your Boyfriend

How to Ask Him to Be Your Boyfriend

A Guy Asks His Roommate If They’re Boyfriends. His Reply Is So Cute!

This is a very cute story about a Reddit user who asks the community for advice about his relationship with his roommate after having come to the conclusion that they might be a bit more than just “friends with benefits”.

The 32-year-old commitment-impaired reddit user “hesmyboyfriend” met his current roommate/boyfriend Alan at a supermarket 18 months ago.

“I’ll be the first to admit, I have huge commitment issues- my parents threw me out for being gay and then shortly after I entered into an abusive relationship with a much older man. After that broke up because he found someone younger, I was inn a relationship with a guy who was in the closet and basically was his dirty secret until he got engaged to a woman without telling me and then wanted me to stick around. I didn’t. After that I became pretty anti relationship,” he says.

They flirted, hooked up and started hanging out together both inside and outside the bedroom. Then Alan’s lease was up and “hesmyboyfriend” asked him if he was interested in becoming his housemate. Alan couldn’t really afford it but they came to an arrangement where Alan would pay what he could, while also contributing by cooking and keeping the house clean.

Related: How to Be a Better Boyfriend to Your Man

“He loves cooking and cleaning anyway, his personality reminds me a lot of Monica from Friends only he works in a library,” he says.

“Before I knew it, I was getting packed lunches every day and he’s made a vegetable patch in the backyard.”

About two months after he moved in, Alan brought up being mutually exclusive “friends with benefits”. “hesmyboyfriend” hadn’t really slept with anyone except Alan for ages anyway so he agreed.

“A few months after that – Alan wanted to join the gym so I added him to my membership as my partner. We turn up to events with each other. We hang out a lot. He sleeps in my room more often than his room because we have sex there the most,” he says.

“Then last week we were at a party when someone asked what our relationship was. Alan laughed, looked at me straight in the eye and said that we were “mutually exclusive, housemates with benefits with income proportional expense sharing”.

“Now that just sounds ridiculous. I know I have a boyfriend, I’ve been sort of denying it all this time but that’s what Alan is.

“This situation is both really screwed up but I’ve also never been happier. He’s so easy to talk to, to hang out with and when he’s not at home I feel bored, like I don’t know what I did with myself before I met him.

“But somehow I both want him to be my boyfriend but a part of me is scared of getting in a relationship, even though I am in one.

“I just feel like saying the words will change everything it’s a commitment and I really want it but there’s that irrational part of me that is scared.

“Also I’m scared that Alan doesn’t think we’re in a relationship even though we are right? Alan has never had a boyfriend as long as I’ve know him and he has his own set of issues too, he’s parents basically tried to “pray away the gay” and he left of his own volition. He used to bring up very subtley about getting more serious but I would just evade and he stopped pushing. It’s so weird, like I can talk to him about everything and anything, we have these amazing conversations but lately this whole boyfriend thing is like the elephant in the room.

“How do I get over this fear of commitment and also what does it say that he’d put up with this crap from me?,” “hesmyboyfriend” asks the Reddit community.

Reddit users replied and urges him to be honest about his feelings. Some suggested that he should cook Alan a meal and then ask him, so that’s what he did.

In an update, he writes:

“It was a bit of a disaster, I screwed up the chicken dish I wanted to make, ended up making mac’n’cheese with this expensive gluten free saffron pasta because Alan is King of the Kitchen and even our olive oil is fancy.

“He was sympathetic but I could tell he was amused when I told him I screwed up the dish and was happy with mac’n’cheese.”

The Reddit user then wanted to pour Alan some wine and ended up knocking his glass into the mac’n’cheese and ruining it.

“So we ended up getting takeaway and watching Netflix and I was still a bit on edge because I’d screwed up the evening- we were cuddling so he could tell that I was a bit tense and not focused I guess.

“Anyway, he asked me what the matter was and I just blurted out “Are you my boyfriend?”, he looked uncertain and said “Yes, if you want me to be” and I just very emphatically said I wanted him to be and he looked very relieved and happy.

“I apologized for evading the topic before and Alan said it was OK because I was the best boyfriend he’d ever had with or without labels and that got us to the fun portion of the night.

“Anyway, a bit later I guess something twigged because he asked me if that was what dinner was about and said yes and he pinched my cheeks and called me adorable.

“Anyway, I asked him if we need to make an announcement or anything but we agreed that we wouldn’t say anything unless people brought it up or we need to introduce each other. Alan also said, he liked the term partner better than boyfriend and I agreed, it does sound more serious but I guess that’s what this is.”

Awwww, so cute!


  1. i thought i found it once or twice but the we got to much on my side to continue! now older and still attracted to the younger man but feel out of luck and lost my place, now I am 50 something and dont feel or look it people say.I need more

  2. I am feeling more than happy than I would have thought….That I ran into this wonderful site ever and for ever ! [edited out] ! Such a wonderful “love story.” I am hoping to find the same some day…either morning or evening of a simple day of the most unexpected, because I happy to be the “born loser.” I am tiring so hard…..maybe too hard? Maybe I’ll meet my match on I feel fine ….really.

  3. I really liked the out come of this because I was reading real fast to find out how it turned out. I thought “hesmyboyfriend” was emotionally immature and another rejection might create a more serious problem. However, it turns out that Alan was a gem of a guy who needs to step up and let his intention known. I believe that dating and petting does not define a relationship however when you enter into something so intimate like sex then a relationship has began. Alan I think will help hesmyboyfriend grow emotionally by being more forth coming and open. My opinion this is the start of something great. Best wishes. I would like to hear what others think.

  4. I am 74 years old and not in the best of health, although it doesn’t show in my physical appearance. I realise that finding a relationship at my age would be difficult to say the least. I am not attracted to old looking guys who keep telling me they’re ‘young at heart’! Recently (last week) I returned from a month’s trip to Amsterdam. On the last night of my stay I visited the ‘gay’ quarter for the first time in fifty years, to see what it was like today. I met two Dutch guys, both professionals and one of them, Willy, (No funny comments please), started to give comments and looks that said quite clearly, ‘I fancy you’. He is 56! I didn’t know what to do. Of course I was flattered and he still persisted even though I made sure he understood how old I am. The long and short of it is that he said he’s making a trip to the UK to see me and asked if he could stay for a few days (He works for KLM airlines). I left it open for him to decide. We have only lightly kissed so far – nothing really sexual. At my age I’m scared at the thought of having something new in my life. I know people might say , ‘Just go for it!’, and that’s exactly what I will do, although I have left the next move up to him. I did fancy him and I think I still do. Are there any older people out there with similar stories where it either worked out or ended in disaster?