Dating at 27: Why Is The “Relationship Talk” So Hard To Have?

Why is answering the dreaded “what are we” so damn dreaded?


Grandparents and French people have a hard time understanding the concept of a relationship’s gray area. To them, you are either with someone or you are not.  The need to define it is ranked about as low as one’s need to “check in” with a clock. It would be like saying, “Clock, what are we doing here? I’m having fun, but it’s 12:00 a.m. Does that mean we’re awake in the early morning, or does it mean we’re up late at night?”

If you’re about to tell me that one could sort of argue in either direction, welcome; you must be twenty-seven.

We’ve all heard the alleged problems with our generation: we have too many choices, too much porn, too much stimulation. Our focus is on building our careers rather than building our future families, and we’re so engrossed in blue screens and various mirrored pools of narcissism that hedonism is our only release. Blah, blah, blah.

Yet I have a hard time believing we’re so cold. I know people my age in relationships. Serious ones. The kinds where you do your whites together on laundry day, meet parents and talk about the future. Having a boyfriend is not a myth; the notion that having the “relationship talk” is what makes you an official girlfriend might be.

I spoke to ten different guys about defining the relationship at 27. That’s a small, statistically insignificant number in the pool of kissing fish, but what they offered was a great insight into the way some straight males think. It’s your call to decide if the guys who perplex you fall into this general bracket.

For the ones I know, it goes something like this:

During the first couple of post-grad years, life is about that new job. Free time is filled with friends. Sexual desire is satiated by sex. Just sex. And in between this, there are dates and fun and flings and even puppy love — but not girlfriends. To them, a girlfriend would be distracting.

Then, around the age of 27, though career and friendship priorities don’t shift, the idea of a girlfriend does. Rather than considering her a distraction, they think of their future girlfriend as someone who could possibly be the last girlfriend, because the next step is getting engaged.

(I know! These guys! So obsessed with marriage!)

So in short — and this can sort of suck: if a guy doesn’t want to define the relationship it could be because he does not think he’s found his wife. He has to be that serious about a girl in order to DTR.

The difference with many straight women — at least those who I know — is that for us, the term “boyfriend” does not mean “you’ll probably be my husband.”

It means: I now know exactly what we are.

Guys don’t have this same need. They are far more comfortable in the gray area.

In fact, they’re so comfortable that one of the reasons they dread “the talk” is because it typically means The End. They can really, really like a girl — but if they’re not 100% sure about the future with her, they don’t want to commit. And they don’t have to…until we say, “Besides me, are you seeing anyone?”

Which is, ultimately, an ultimatum.

For your sake and the sake of honesty, this is a good thing. If you feel weird about the situation, if you’re no longer comfy in the ambiguity, speak your mind. Clear the air. Be prepared for the “wrong answer,” but then you’re free to move on — Beyoncé, should you take this or should I? — to someone who is 100% about you. Fuck the waffling; you’re not a toaster.

Another (lesser) fear these guys have is that when the word “boyfriend” is pinned to their shirts, things change, you stop having fun, fights start and everyone has to act differently. My friend Monty said, “It’s been five years since I’ve been in a relationship. How do I even know how to be a boyfriend?”

Another friend, Casey, offered a bit of insight: “We can feel backed into a corner when you bring up ‘the talk,’ like we’re being accused of something and about to get in trouble.” He suggested trying to figure out where the guy’s mind is headed instead. “Ask him questions about where he sees himself in a few years. What does his life look like? Does it involve a move? Slowing down the partying? A family?”

Isaac Hidin-Miller says this a lot in his Ask a Guy column, but you have to believe people when they tell you exactly who they are.

See if you align and go from there.

“Defining the relationship should feel like a mutual, positive, logical next step,” my friend Bret said. “What it shouldn’t be is a reaction to a worry. If there’s a worry, then address the problem. Defining a title won’t fix anything.”

This makes sense. It’s like buying a puppy to solve a fight. Still, I cannot tell you how many times I repeated to these guys, “SO WHEN. DO YOU HAVE. THE TALK? AND HOW?”

All of them — from California to South Carolina — responded with the same, infuriating, frustrating answer: “It just happens naturally. When you know, you know.”

Men: more romantic than anyone gives them credit for, with conclusive love advice eerily similar to that of my grandma.

All names of those interviewed and quoted have been changed. Gif illustrated by Emily Zirimis. 


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  • Haley Nahman

    One time in college I decided on a whim to introduce a dude as my boyfriend prior to any agreements. SURPRISE! Do not recommend.

    • rachel

      My I had a boyfriend do exactly the same thing! Or close, he didn’t call me his girlfriend in front of me but as I was walking up to his apartment I heard him tell his friend he was “waiting for his girlfriend.” It didn’t freak me out really (I’m a serial monogamist so I wasn’t dating anyone else anyway) but it was a little off putting. I didn’t say anything about it, but the next week as we were falling asleep he asked me if I wanted to be exclusive with him. We are fast approaching our three year anniversary, so I think you can guess what my answer was… 🙂

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      • Rosie

        Ha! A similar thing happened with a past boyfriend of mine — we were on the phone about 3 weeks into hanging out and he said something like “my little brother was surprised to hear that I have a girlfriend.” And I was all like, OH DO YOU? Lol. We’re not together anymore, but that’s one way to do it!

  • “When you know, you know.” An old adage I’ve yet to come to terms with.

    • Kay

      I don’t know where the surveyed guys were in their dating life, but had they actually had the “you know” experience, or were they saying what they thought would happen when they met their dream girl one mystical day? Maybe they really just aren’t confident about relationships and feel lame saying that out loud. This is cynical, but it seems like the inexplicable “knowing” keeps the relationship power on their side forever. Like why does it have to be “the one” before a guy can agree monogamy?

    • sometimes you think you know but then you actually don’t. I can’t be the only one, right?

    • As someone who was grossed out by the idea of commitment until I fell into a “when you know, you know” situation, I think it holds some weight.

  • Savannah

    Perfect timing. I just re-read Amelia’s piece on the avocado theory last night, too. Guys, can I ask for some advice here?

    • Amelia Diamond

      yes! ask!

      • Savannah

        Ok so I (25) saw this guy (31) I met through a certain app this weekend and after months of texting back and forth, I agreed to come to his house for a hook up. He already told me not to invest too much time in him when we starting texting, as he wasn’t looking to date now. I appreciated the honesty and it seemed simple and clear (I was trying to give this casual sex thing a shot) – but it turned out to be the complete opposite. We talked for hours, it was really good conversation and even though we’re practically strangers both of us were really comfortable. We both exceeded each others expectations and both of us admitted that explicitly. We did end up sleeping together nonetheless – that was the premise of our meeting after all. Afterwards we talked again for hours, more stuff happened and the next morning I left feeling super confused. What the hell did I do? I haven’t connected with a guy like this since 2 years probably and I can’t stop thinking about him. I can’t turn back time, but now what?
        Disclaimer: I know this has so little to do with an issue like ‘when do you have The Talk’, I know. Sorry Amelia!

        • Amelia Diamond

          This is your answer: “He already told me not to invest too much time in him when we starting texting, as he wasn’t looking to date now.” People are surprisingly honest. We (all) like to interpret what they tell us to help our own narratives along. Believe people when they tell you that they “aren’t looking to date right now.”

          That doesn’t mean people’s feelings don’t change. His could! But it’s never something to bank on or wait around for, and if you haven’t heard from him, it’s 100% because he wanted to keep it at your original agreement: just sex.

          NOW. Just because it was “just sex” doesn’t mean you didn’t also connect. I bet you did. It sounds like you did! And as we get older it becomes more and more rare that you find people who really spark you in a ways that cause you to pause. That’s special and wonderful (especially if you’ve been asking yourself: “Can I feel that way anymore?” because you can) but it doesn’t mean it’s a guaranteed start to something more.

          You could do two things: 1) Accept that this was a wonderful and fun experience. The happy end! 2) Reach out well-knowing he might say no, or, that he might say yes for the interest of more sex (and just sex), OR 3) that there’s a slight possibility (teeny, small, again: trust his honesty) that he’s open to changing his mind. Say something like, “I know you said you’re not looking to date but I really enjoyed our conversation. Any interest in a drink?”

          But again, I go back to my first point: he already gave you his bottom line.

          • Savannah

            Thanks, really appreciate this. Deep down I do realize this has a one percent chance of a fairytale ending (why do we keep watching rom coms again??), but still. If it does happen though, you guys will be the first to know haha! And another thing; I think all the articles you guys post on these topics are SO GOOD. Well done.

          • Aydan

            Amelia’s advice is spot on! Additionally, I’d add, don’t be hesitant about reaching out again if that’s what you want. I’m a firm believer that if YOU want to see someone again, then take the steps to make that happen. If they don’t want to see you, so be it, but you tried!

          • If you reach out they probably think they are so good in bed that you want more.

          • To you it could be the perfect match, to him it could be just the perfect date! We always think long term even after we met someone once. Like, you don’t actually know him that well.

            Don’t waste too much energy thinking about things like this, you need to invest your time in loving yourself and give you your own fairy tale then ruling the world first! 😀

        • “He already told me not to invest too much time in him when we starting texting, as he wasn’t looking to date now.”

          I’m a firm believer that somebody needs to want to be in a relationship before they meet you. I think we all have a fantasy that we’ll be the special someone to change somebody’s stance on commitment. I don’t think you necessarily prevented a relationship from developing by sleeping with him – but you will essentially tell him that you’re cool with a casual, noncommittal arrangement if you continue to sleep with him.

          “We both exceeded each others expectations and both of us admitted that explicitly.”

          Like Issac always says, if a guy wants to see you, he’ll try his best to see you. It’s very likely that he was also surprised by how much he connected with you. If you don’t hear back from him, please do not blame yourself or the fact that you slept with him.

        • rachel

          I have been in a similar situation, and while we didn’t end up dating, it was really amazing to have a friends with benefits situation with someone I actually connected with. If you think that’s something you could be okay with it could turn out to be a great and fun experience for you– as long as you are okay with the knowledge that it will end when one of you finds someone else, and him finding another girl doesn’t have anything to do with you. By the same token, you need to make sure he’s comfortable with the idea of you finding someone else and leaving the hooking up behind. I unfortunately did not make that clear with my guy and he ended up really hurt when I moved on to a real relationship, even though it had nothing to do with him or any faults he had. Best of luck with whatever you decide to do!

          • Alison

            “When someone shows you who they are, believe them.” — Maya Angelou (the first time)

      • RaquelT18

        Omg I tell my friends about the avocado theory all the time! one of the most epic blog posts

  • rosa fairfield

    Really interesting article. I’m going to send this over to my friend, who is having relationship trouble right now. It could explain a lot for her.

    • Amelia Diamond

      Let me know how it goes

  • estheresther
    • Amelia Diamond

      Oh my god no, and I can’t wait to!

  • You’re in a relationship with someone regardless of whether or not you use words like “boyfriend” and “girlfriend.”

    The way we approach dating and project onto the word “relationship” baffles me. There’s so much fear of scaring somebody away and anxiety about the future. When I was single all the advice I received was to remain passive, and not tell someone that I was interested in them.

  • Whoa, this is great timing.

    My friends are often concern with my situation and asking questions such as, “Did he ask you to be his girlfriend?” That formality never happened.

    We both know we aren’t seeing other people and we naturally became exclusive. Titles are often confusing, too. IDK, I have learned to let go of it a little, and trust the person.

    So you are right, “When you know, you know.”

    Love this. Thank you MR!

    Big Fan,

    • Amelia Diamond


  • Natalie
    • Aydan

      that really resonated with me!!

      • Amelia Diamond

        and the GIF with me

    • Lillian

      I need this emblazoned on my forehead.

    • Rosie

      YES. Was just about to call out the same quote! Fucking perfect

  • Aydan

    Honestly this is soooo timely! I’m in a slightly bizarre situation with a friend I recently reconnected with. Obviously all the fun 26 year old stuff is happening but we are also newly minted good friends. He broke up with his ex gf two months ago (aka not emotionally available). I’ve been happily operating in this grey area for some time with a few people over the past couple of years, so this is my happy place for the point of my life I’m in (I know this is not for everyone). Yesterday he CALLED me as he was leaving his therapist appointment to ensure that the two of us are on the same page. He was concerned I wanted more (WHY DO BOYS ALWAYS JUMP TO THIS CONCLUSION?!) Full disclosure, we had discussed the no string attached nature previously, but being able to say on the phone yes we’re on the same page and here are my two rules: 1) tell me if you sleep with others (cause you know health reasons) 2) I want to continue being friends whether or not the other bits cease. He agreed and let me tell you it is liberating to have full disclosure whatever it that may mean to you!

  • Ashley

    It freaks me out that you keep writing posts specifically about my life

    • Amelia Diamond

      we live in your brains! jk you guys live in ours I think

  • Jolie

    Wow, this is so spot-on, and a great insight into something that happens all too often. I once had an ex who told me at the beginning of the relationship that he had never been in love with anyone before, almost like a warning. Within a couple of months, he had told me he loved me. I thought that we were very solid as a couple by that point, but we hadn’t had “the talk” in any formal way. When that started to frustrate me, I brought it up, and the relationship effectively ended there, even though we dated for months after that. It’s like the emotional availability stopped at the talk. I think even IF someone is being exclusive with you, once you talk about it, they can start to feel like the relationship is being examined and are no longer 100% in it.

    I also think this article really ties into your thoughts on being “chill” in a dating situation. We as women sometimes feel pressured to be chill and not have the talk, in order to keep that sense of “I think we are what I want to be, so let’s not ruin it.” Great job, Amelia!!

  • Lebanese Blonde

    Does anyone else give off perma-girlfriend vibes? I’ve only had one serious boyfriend (still in my early 20’s) but still, every man I ever meet gives me the unprompted “I really like you but I’m not trying to date anyone right now” spiel. Which is disheartening if I’m more into them, but 99% of the time my answer is “SAME, K?”

    Somehow, no matter what I do (save completely ignoring someone), men assume I’m planning our wedding. No one believes I want a casual thing ever, even if I genuinely do! It is infuriating! I speculate it’s a combination of my good-girl/friendly/responsive qualities. How do I banish this perception, o’ wise Amelia? Save pretending to just be a bitch?

    • Elliot Faulk

      Find a nice guy? Honestly then again I might be rare.

  • Maddie McDonald

    “Fuck the waffling; you’re not a toaster.” is probably my favorite line on MR to date

  • Anna

    This is tooooooo perfect and so funny! Loved it 🙂

  • About the French : I am french and my dating life is one big grey area !

  • very nice article. I am glad to read this. thanks for sharing with us.

  • This is a really interesting read, especially for someone who at 29 has just come out of a relationship due to my 35 year old ex “not feeling the same anymore”! x

  • Margot

    As for so many others, this is so relevant to me, so thank you! I have also been embroiled in that grey-area world of friends with benefits, having had ‘the talk’ some months ago. This went something along the lines of, ‘You’re great, we have so much in common, I’ve liked you for a long time, but I’m just not ready for anything serious…’ I guess what I’ve struggled with is the curious lack of intimacy. We message almost daily, he has incorporated me into his group of friends (to an extent), and I know he has a real affection for me. Yet when it comes to sex it really is just sex, and even then I’m not entirely sure when he wants it and when he just wants to spend an evening as friends – I’m beginning to feel a bit powerless in that regard. So we inhabit this strange realm where we can be good friends, and sexual partners, and yet we are fundamentally missing out on those things that I think a lot of us want out of a relationship. Articulating this in writing, it now seems obvious that I’ve fallen for what some of you have already pointed out – that when a guy says he’s not looking for a relationship, he really isn’t. I suppose I’ve just never met anyone who is still able to foster such a close friendship at the same time!

  • doublecurl

    My now boyfriend and I traveled to NYC together early on, where my friend introduced him to her group as my boyfriend. Then he was my boyfriend. Ace move by the friend, highly recommend.

    • Katherine Sargeant

      I love that story

    • Agreed! My now boyfriend and I had been seeing each other regularly for about a month. We went to a party with some of my other guy friends and some girls started flirting with them, and one of the girls said “don’t worry I’ll leave your boyfriend alone” to me and that was that. The guy I was seeing before him wasn’t as great though. We would hang out with his friends and they would call me his girlfriend but he still refused to give me the title.

  • The grey area is so nerve-wrecking. But I wonder why girls feel so much more uncomfortable in it. I’d always attributed this to the societal pressures that dictate that we must constantly be on the lookout for The One but that’s in direct contradiction with how you say women view the ‘boyfriend’ label.

    • John

      Because you care and we don’t. Next.

  • F.

    This is exactly my life right now. Great guy, great relationship (we’re both 27 btw) but WHAT ARE WE??? I really wish I could be more “french” and less interested in relationship titles, because it really adds some -completely unnecessary- anxiety to the relationship. Probably anxieties just in my head though, because he seems perfectly happy and content.

    • John

      You can’t help it – you’re female and you crave drama. Just find someone else. Next.

  • ms.g

    I don’t buy the “it happens naturally…” thing. There is definitely some good advice in the article like if something is worrying you talk about that. Defining things won’t necessarily make that worry go away. However, my issue here is that we let guys (straight ones that is) off the hook a too much. They need to step up and say where they are at with things. If they aren’t 100% or they need things to go slower or whatever…they need to say that. Too much is put on women trying to figure out what a guy is thinking or just go with the flow. Women for are part also need to communicate where they are with things and so forth. However, we have become afraid to do that b.c. we’ve been bombarded with the message that “happen naturally..” message. That message allows both men and women to not take responsibility for their actions towards another person. It’s a choice two people make. And it’s a choice you keep making.

  • Martyna

    Honestly, it feels like girls have to tiptoe around guys, because – oh dear god – they might feel uncomfortable or get scared. I call BS. You need to be open and honest. If a guy is waffling and you want something serious, time to walk away.

    • John


  • Holly Keiser

    What do you do when you HAVE brought it up after dating 5 months and he actually told you he really likes you, but he’s just not sure if he can see long term with you? We’re still seeing each other, I really like him.. but I feel very weird/confused after being told that.. I know this post was 6 months ago, but any advice?

    • Zoë

      Sounds like he wants to have his cake and eat it too. I’ve been there.. I decided I want to be with someone who is sure they want to be with me. As much as I liked the guy, I ended it because we wanted different things.

    • John

      It means he doesn’t want to be with you long-term. Next. (smh)

  • Holly Laine Mascaro

    My current boyfriend and I never actually had that conversation haha…once after months of dating he was calling Time Warner Cable for me and when they asked him what his relation to me was, I saw him look over at me sheepishly and go: “Uhhhh….her boyfriend?” BUT what I do highly recommend as a happy medium here, is instead of having the “are you my boyfriend?” conversation, I make it very much about the physical logistics rather than defining things emotionally. Meaning, when we get to that inevitable moment where we have been seeing each other for a while, are physically intimate and may now want to reconsider the level of protection that’s being used, that’s when I use the opportunity to say: “I am open to this as long as we agree we aren’t seeing anyone else.” That way, it takes the pressure off emotionally but you can both feel secure that you’re the only people you’re seeing – and feel physically secure as well! Obviously trust is a key factor here – but isn’t it always.

  • John

    If you don’t like the gray area, then GET OUT OF THE GRAY AREA! I get so sick of women’s complaints in relationships. If you don’t know where you are, ASK HIM! If he doesn’t give you the answer you want, DUMP HIM! It really is that simple. Yes I am comfortable in the gray area, but that doesn’t mean you have to be. If I sense a woman is getting all anxious and needy about our status, and she isn’t woman enough to bring it up, I’ll do us both a favor and dump her first. It seems most women would rather hang around the fringes and passively nag us to get married. If I guy wants to marry you, he’ll do it quickly. If he doesn’t, there’s nothing you can do about it. SO QUIT COMPLAINING!