Dating a close guy friend

Dating a friend is widely recognized to be a pursuit fraught with potential complications. If it works out, great — but if it doesn’t, well, there’s a good chance the friendship won’t survive unscathed. I learned this lesson the hard way when I started dating a friend in high school. Not only were we good friends, but our families were also extremely close and had been for years.

When we broke up nine months later, all the usual post-breakup awkwardness and bitterness were multiplied tenfold by the fact that we were forced to hang out whenever our families got together, which was often.

On the flip side, when we rekindled the flame after college, our friendship and the friendship between our families became one of the best parts about our more-than-friendship. We had a shared history, our siblings adored each other and we even went on a few joint-family vacations.

Having personally experienced both the positives and the negatives of dating a friend, I’ll say this: there are few things more precious than a friendship that becomes more than a friendship, but there are also few things more painful than losing a romantic relationship and a friendship simultaneously. The stakes are uniquely high.

To commemorate the end of Friendship Month at Man Repeller, I interviewed five couples who braved the stakes and went from “friends” to “more than friends.” Below, their thoughts on what that leap was like.

Ashley and Kelly

How long were you friends before you became “more than friends”?

Kelly: We were good ol’ fashion friends from the fall of 2010 to the fall of 2011. We started dating in the fall of 2011. Then we were friends with benefits until I moved to Seattle, and then back to just friends until October of 2013.

Ashley: We met in a college class and slowly became friends. He made me laugh a lot, but I was very suspicious of him. He seemed mischievous in a way I wasn’t. And he was a white boy with a slight country accent who drove a pick-up truck. I assumed he’d be more into a woman who reminded him of Taylor Swift.

How long have you been together as “more than friends”?

Ashley: We hooked up for a semester in college, then spent about two years being mostly just friends again while he did an internship in NY (I was still based in Indiana) then moved to Seattle. After a year in Seattle he came back to Indiana to visit, and we decided to try and date for real. That was about three and a half years ago.

Was the transition a weird at first, or completely natural/inevitable-feeling?

Ashley: We talked so much about every decision and all of our feelings so that even when it felt weird, it quickly went back to not feeling weird. When he showed up in Indiana the last time, I was terrified to try and date ANYBODY for real. But it quickly felt natural and right after all that talking and sharing.

Kelly: I believe we handled the evolution of our relationship very consciously. Nothing felt weird to me, but the transitions didn’t just happen on their own. At each new point, we always had a conversation to find out where we were and how we felt.

What’s your couple backstory?

Ashley: We met in a seminar that was set up like a production company, and I was his boss. We had a good time together as buds. About a year later, after ending a terrible relationship and getting fired from my job, I went to a party at his house. He asked if anybody wanted to go four-wheeling, and I said I did. That ended up being our first date.

Kelly: She didn’t really know it was supposed to be a date.

Ashley: The second time around, after he’d lived in Seattle, he just showed up on my doorstep and kissed me. Then he asked if I was seeing anybody. We’ve been together since that day.

Do you believe in the When Harry Met Sally adage that two people who are attracted to each other can’t stay “just friends”?

Ashley: I’m bisexual, and if this were true, I wouldn’t have any friends. I think all of my friends are hot. And I have been attracted to most of them at some point or another, just not in a way that I could or wanted to sustain. So, I didn’t.

Kelly: I think that viewing relationships as an inevitable thing that happens between two people who are attracted to each other takes away from the emotional vulnerability, and work, that goes into building strong commitments. Also, it really doesn’t say much for platonic friendship if you can only be friends with people you aren’t attracted to.

What’s the best part (or parts) about dating/being engaged or married to your friend?

Kelly: The person I want to hang out with most is right next to me when I wake up.

Ashley: No matter where I am or what I’m doing, if I’m with Kel, we can turn it into a good time. We don’t just like each other, we also like A LOT of the same stuff. And we introduce each other to new things all the time. Plus, he’s fun to talk to about anything because he’s animated, opinionated and hilarious.

Any drawbacks?

Kelly: Well, you spend as much time together as you possibly can, eventually you get irritated for pretty much no reason.

Ashley: We sometimes get stuck in our little bubble, just seeing each other, just talking to each other, just hanging out together, and it’s fun for a really long time. Until it isn’t. Then we’re annoyed with each other. One of our goals this year is to spend more time with other people because we need that to avoid some of those moments when we’re staring at each other and thinking, “OMG, GO AWAY!”

What advice would you give to someone who’s started developing feelings for a friend?

Kelly: Talk to your friend, see how they feel, and go from there. Be prepared for it not to go your way and that being just friends with this person is probably a whole lot better than not knowing them anymore.

Ashley: Take your time with the feeling, and prepare yourself to be extremely vulnerable. Also, if your friend doesn’t share those feelings, don’t be angry with them. This isn’t a betrayal. It’s just a difference in feeling. Try to know if you can live with that, and if you can’t, be honest about it.

Maggie and Brice

How long were you friends before you became “more than friends”?

Maggie: Almost a decade. He was always the standard against which I measured other men, and we dated a bit when we were younger. I would have liked it to be more then, but it wasn’t, so we became friends. I was always very proud to call him a friend.

Brice: I always harbored a greater appreciation and respect for Maggie than “just a friend.”

How long have you been together as “more than friends”?

Maggie: The best year of my life. (So far.)

Brice: We could say we’ve been together for a year, but we could also say we’ve not been apart for eight or nine or 10 in many ways.

Was the transition weird at first, or completely natural/inevitable-feeling?

Maggie: Brice had moved to LA. I was in New York, building AYR. The company had just gone through some big milestones and I was totally fried. Pretty much out of the blue, he said, ‘Look, I need to get out of town. I’m booking a flight to New Orleans for this weekend. Are you coming?’ I didn’t even think about it. We both needed an adventure. The moment we saw each other – we hadn’t seen each other in a while – it was on. It felt like being on drugs. Everything was The Best. I was struck by this visceral sensation, like ‘This is The Point. Of being alive.’ It was real life, better than I could have imagined. It just made total sense, and was a complete surprise at the same time.

Brice: I should have been with Maggie since ’08, but then again, I suspect I am better because of the experiences in between. I’m certain she, recalling ’08 Brice, would agree. A decade of dating in NYC can teach you a lot about yourself.

What’s your couple backstory? 

Brice: [Defers to Maggie]

Maggie: We met at our first job. We both went to work for J.Crew straight out of school – he was in men’s design, I was in women’s merchandising. We sought each other out, dated, then became friends. We were friends for a long time. We’d find ourselves in the same city – Los Angeles, or Paris – because of our work, and we’d catch up. I’d ask him for career advice, he’d ask me for relationship advice. We dated different people, made other friends, had our own adventures, grew up.

Do you believe in the When Harry Met Sally adage that two people who are attracted to each other can’t stay “just friends”?

Brice: I don’t subscribe to that belief. That adage is sweeping and reductive. I respect friendship more than a fleeting escapade. That being said, yes, some people (read: men) can’t not try and sleep with their attractive female “friends,” I’m just not that guy.

Maggie: I believe in it to the extent that when you realize you want to spend the rest of your life with somebody, you want the rest of your life to start as soon as possible. Also, that Mallomars are the greatest cookie of all time.

What’s the best part (or parts) about dating/being engaged or married to your friend?

Brice: Fundamentally, I believe a partner — be they husband, wife, girlfriend or boyfriend — is first and foremost a friend. If the characteristics of a good partner were depicted in a word cloud, with the most important characteristics being the biggest, “friend” should overshadow the rest. In my past relationships, it didn’t, and ultimately that’s why they didn’t work out. The relationships I admire most are ones in which both people are freakishly into each other, and the way they communicate — their humor, their empathy — is mirrored equally. Being with Maggie, I’m having that experience for the first time.

Maggie: Before I got together with Brice, I’d actually been saying for a while that I needed to date someone who ‘already knows me.’ Who I am is not for everyone, but I have no interest in being anything other than myself. I think the best thing about falling in love with a friend is that you both go into it with complete acceptance – and appreciation and admiration – for each other. There’s a level of security, confidence and comfort that’s impossible to create in an instant. Those things have to be earned, built over time. We were lucky to start with that base.

Any drawbacks?

Brice: Nope.
Maggie: Nope.

What advice would you give to someone who’s started developing feelings for a friend?

Brice: Do something about it.
Maggie: Book a flight to New Orleans.

Dom and Nick

How long were you friends before you became “more than friends”?

Dom: We were friends for about three years before before we became “more than friends.” We met as teenagers and hung out a few times but mainly kept in touch via Myspace (yes Myspace, haha) and Facebook.

Nick: I really credit social media with allowing us to even have a friendship. We didn’t go to the same school or live in the same neighborhood, so if we weren’t able to communicate via Myspace and AIM, who knows if we would’ve reconnected later and started dating?

How long have you been together as “more than friends”?

Dom: We reconnected in person on the weekend of Fourth of July in 2010. Nick was visiting Orlando to help a friend move into her college dorm. I was going into my junior year at the same university, and Nick reached out to me and asked if I wanted to hang out. We hadn’t seen each other for at least two years, but I’d never forgotten the kinship we had when we met as teenagers, so I said sure. Things moved quickly after we met up. We decided we wanted to be “more than friends,” and on July 17th, we officially got together. We’ve been pretty much inseparable for the past seven years.

Was the transition weird at first, or completely natural/inevitable-feeling?

Dom: The transition was both natural and inevitable-feeling. From the very beginning, we realized how much we had in common, and how similar our life plans were. It’s rare to feel such a deep physical, emotional and spiritual connection with someone at such a young age. I knew there was something special between us.

Nick: Ironically, the weirdest thing about dating each other was discovering how much we actually had in common. We are both obsessed with the show Girlfriends (from the early 2000s) and can quote it endlessly. We also both prefer to watch movies with subtitles, which is so odd and we both hesitated before admitting it to each other.

What’s your couple backstory?

Dom: Six out of the seven years we’ve been together were long-distance. As I mentioned, we started dating in July of 2010, and Nick moved to Kentucky for college that August. We spent the entire night before he moved away to college cuddled on the steps of a lifeguard house on the beach (we went there often at night to talk and listen to the ocean), and I remember telling him, “We will be good. We will be better than good. We will be great.” Since that night, we have always gotten through rough times in our relationship by saying those words to each other, and truly believing them. For six years, the closest we lived was a four-hour bus ride between D.C. and New York, and the farthest we lived was a seven-hour flight between London and New York. The weeks and months we spent apart felt like centuries, and the short weekends and long holidays we spent together felt like minutes, but every time we got to see each other, I was reminded of why I would wait a lifetime to spend just a moment with Nick.

Nick: I’ll add that while the long-distance aspect could have weakened our relationship, it actually strengthened it. It forced us to appreciate the little thing (calls, texts etc.) and cherish the limited in-person time we had when we were together. When you spend every day together, it’s easy to overlook that kind of stuff.

Do you believe in the When Harry Met Sally adage that two people who are attracted to each other can’t stay “just friends”?

Dom: No, I think two people who are attracted to each other can stay “just friends.” Building and nurturing a relationship that survives all the hiccups is not as easy as movies lead us to believe. It requires purposeful, consistent attention in addition to care, patience, understanding, willingness to grow and compromise. The initial attraction is just the tip of the iceberg.

Nick: I agree. I think you can be attracted to multiple people over the course of your life, but it’s all about timing. If you have a strong connection with someone and the timing is right, there’s a better chance that attraction could lead to more. Dom and I could have stayed friends forever, but the timing to take it beyond that was right for us.

What’s the best part (or parts) about dating/being engaged or married to your friend?

Dom: Knowing I have the space and security to be imperfectly me. When I am with Nick, I know that I can make mistakes. I can be corny, I can be wrong (he actually loves when I’m wrong, haha) and I can be who I am. As a black man, especially one of Caribbean descent, there are harsh pressures to conform to a variety of heteronormative conceptions about masculinity, but that rubric doesn’t leave room for my entire identity. The relationship Nick and I have built is strong enough to withstand those pressures and allows us to be ourselves, unapologetically.

Nick: Planning a wedding is also so much more fun when you’re engaged to someone who’s first and foremost your friend. We both enjoy the same style of party, so we haven’t had any disagreement or clashes. To me, the seamlessness of this process so far is further proof that I am marrying the right guy.

Any drawbacks?

Dom: Sharing the bathroom and the mirror.
Nick: Ditto. We really need a bigger bathroom.

What advice would you give to someone who’s started developing feelings for a friend?

Dom: Ask yourself what you’re looking for (e.g. A relationship? Marriage? A friends-with-benefits situation?). You may not know what you want, which is okay, but you should still communicate that to this person and find out what they want. Be open and honest, and communicate as much as possible.

Nick: Tell them! It’s always sad to hear a story in which one friend is hopelessly pining after another but hasn’t told them. If you don’t speak up, you’re either robbing yourself of a “more than friends” relationship with that person, or you’re robbing yourself of the chance to move on if they don’t reciprocate your feelings.

Amanda and Hans

How long were you friends before you became “more than friends”?

Amanda: Six months.

Hans: An intense six months. We met while studying abroad in Cape Town. We lived in the same house full of international students.

How long have you been together as “more than friends”?

Amanda: Eight years?
Hans: That sounds about right.

Was the transition a weird at first, or completely natural/inevitable-feeling?

Hans: It definitely felt inevitable, but it was a bit weird at first. We were so close as friends and spent a lot of time together. Plus, we were traveling and working in East Africa, so it was sort of a sensory overload to begin with. I guess I’m drawn to taking on lot at once.

Amanda: Definitely inevitable, but there were a few awkward moments in the beginning we laugh about now.

What’s your couple backstory?

Hans: I’ll pick up where we left off in Cape Town. The semester was coming to an end and we grew super close as friends, so we each separately devised ways to stay together longer — like we both got internships in Nairobi.

Amanda: I had a big crush on Hans and all of our friends knew — except Hans, of course. I devised a trip to East Africa and invited him to come along. He didn’t hesitate.

Hans: On our way to Nairobi, we traveled through Tanzania to Zanzibar (otherwise known as the most postcard-perfect romantic spot in the world). That’s where we became more than friends.

Amanda: I remember messaging my friends and saying, “Guys, it FINALLY happened.”

Do you believe in the When Harry Met Sally adage that two people who are attracted to each other can’t stay “just friends”?

Amanda: There was a natural attraction, but to stay more than friends, we had to make a conscious choice to make it work. There were so many difficult factors. I lived in Vancouver, he was living in Wisconsin, etc. We didn’t just fall into a relationship — it took work. And still does!

Hans: I don’t really believe in what Billy Crystal a.k.a. Harry said. I think people can be attracted to one another and stay friends. There are lots of attractive people in the world, and it’s not hard to make friendly small talk about bagels or the weather, but finding true compatibility is a whole different ballgame.

Amanda: Still great dialogue in that movie.

Hans: And City Slickers was okay.

What’s the best part (or parts) about dating/being engaged or married to your friend?

Hans: We laugh a lot and share so many memories. Does that apply to every couple, though? Since we were friends first, there was never a “first date” vibe — we kind of went straight into the good stuff.

Amanda: We share so many friendships that we built before we were “together.” It’s really nice to have people in our lives that have known us separately as individuals and together as a couple.

Hans: Everyone likes her more.

Any drawbacks?

Hans: None really come to mind for me. Even though we were friends for a while, there was always an attraction and a courtship even if it was through the channel of friendship. I was more subtle and strategic, but Amanda was pretty blunt. The first thing she ever said to me when we met around a crowded dinner table was, “Wow, you smell nice.” She said it just a bit too loudly, so everyone heard and stopped talking and laughed. That’s when I knew we would be more than just friends, but it took a while. The delay was definitely a drawback.

Amanda: I didn’t know we would be more than friends. I just thought you smelled good.

What advice would you give to someone who’s started developing feelings for a friend?

Amanda: It’s a high-risk, high-reward scenario. Keep that in mind before you go for it.

Hans: If you’re developing feelings for a friend, take it slow and easy. Explore those feelings and spend lots of time getting to know the different sides of your friend before you make a move. Try to spend time with them in all types of situations — not just the fun ones. You’ll get a better idea of what type of partner they’ll make. We took a road trip with a few other friends early on, and we had to do a lot of problem-solving.

Amanda: Definitely travel together. It’s the quickest way to see different sides of someone’s personality.

Hans: Amanda held it down on our road trip. We got a flat tire on a dirt road in Namibia while driving a very ill-equipped Volkswagen. We changed the tire together, then dug the car out of what was actually quicksand a few days later. Best of all, we somehow kept our damage deposit.

Amanda: On all of our adventures Hans keeps us laughing, even when there are hiccups and flat tires.

Hans: If you can find a friend like that who you’re attracted to, make a move.

Jill and Alex

How long were you friends before you became “more than friends”?

Alex: We met the summer heading into high school.
Jill: And quickly became best friends, so we were “just friends” for about eight years.

How long have you been together as “more than friends”?

Jill: Eight years now!
Alex: It finally happened during the summer of 2009.

Was the transition weird at first, or completely natural/inevitable-feeling?

Alex: At first there was some hesitancy because of our friendship and our shared group of friends. Other than that it was felt very natural.

Jill: Yeah, it felt pretty inevitable for me, too. There were times during both high school and college that we almost dated, so when we finally got together it was exciting. As Alex alluded, the only tricky was announcing that we were dating, because we shared the same core group of friends (although most of them claimed to sense that they already knew it was going to happen.)

Alex: It didn’t really surprise too many people.

What’s your couple backstory?

Alex: After we met the summer heading into high school, we quickly fell into the same group of friends (and we’re all still friends to this day). We were definitely close throughout high school, but we never crossed the line beyond friendship.

Jill: We were freshman gym-class square-dancing partners, though! (Yes, that actually happened). Honestly, there’s never been a time when I haven’t felt comfortable with Alex. I think we’ve always shared a mutual attraction (I for sure had a crush), and as far back as I can remember, we were remained close. We almost dated once in high school and again during college, but we ended up with other people instead. Even so, we still visited each other in college and spent time together whenever we were on vacation from school, so the friendship component was always there.

Alex: After college, we were both single again, and I was getting my masters at Temple University in Philadelphia while Jill was living and working in New York. I started visiting her as often as I could, despite working full-time and finishing school. Once I graduated, I made a serious effort to find a job in New York so we could move in together. That’s when it all fell into place.

Jill: Once we finally became “more than friends,” we never looked back.

Alex: We’ve lived in the same apartment on the Upper East Side ever since, and the neighborhood has been a big part of our lives. It’s like a map that shows the history of our relationship, from our favorite bars and restaurants to the spot in Central Park where I proposed to her.

Do you believe in the When Harry Met Sally adage that two people who are attracted to each other can’t stay “just friends”?

Jill: Nah, I think that’s silly. I believe if there’s a certain level of maturity, you can be attracted to someone and remain friends. People tend to see it as very black and white, but I think there can be a blur to the line.

Alex: I’m going to be honest and say I’ve never seen the movie, but the idea makes sense I suppose.

What’s the best part (or parts) about dating/being engaged or married to your friend?

Jill: There are so many, but the first thing that always comes to mind is that it’s just so easy. When we moved in together, I expected this huge emotional ‘shift’ or weird feeling to set in that I’d have to try and kick, but it was totally seamless, as if we’d always been living together. We were already aware of each other’s emotional ins and outs, so we knew how to have hard conversations without yelling or fighting. There’s always a certain level honesty that’s built-in. Also, because there’s such a solid friendship at the base of our relationship, we genuinely love spending time together and can have as much fun alone as we do with groups of friends. We’ve basically grown up with one another, so there’s a silliness to our behavior when we’re together (my mother frequently shakes her head at us). Alex is my safe space, the person I turn to in order to get away from everything else. There’s no one we look out for more than one another. In the end, I think that a love based in friendship is a deeper kind of love, one that I didn’t know existed until I experienced it.

Alex: Jill knows the real me. There’s no hiding. It keeps me honest but also allows me to open up more and build on that preexisting foundation. It can be tough to open up to someone you’ve only just started dating, but when you’ve already been friends with someone for almost 10 years, there’s really no going backward. Just thinking about all of the things you’ve said and done in front of this person makes any new stuff less intimidating to share. I think our rhythm and rapport are the two things I love most about our relationship, but I am not always conscious of either, because both have always come so easily thanks to our friendship.

Any drawbacks?

Jill: Not for me.
Alex: Nope.

What advice would you give to someone who’s started developing feelings for a friend?

Jill: There are a lot of variables. The longer you’ve been friends, the trickier it can be — but also the more rewarding. You just have to be honest and open with one another the whole way through. That’s key. If you’re compatible enough to be friends, and you have a mutual attraction, the risk of crossing that line can absolutely be worth it.

Alex: Don’t question it, but be prepared for things to get serious fast.

Photos by Savanna Ruedy and Edith Young.