“How Do You Know If You Love Someone?”

I’m currently dating a guy whom I’ve known for seventeen years. We have always been in other relationships and this is the first time that we have both been single and able to see if we are compatible, etc. We have been seeing each other for a little over four months. He spends almost every night at my house, we spend a lot of time together, and we get along great. But neither of us has said “I love you.” I felt like saying it a few times but didn’t, and then the moment passed. We were both in long-term relationships before and we have known each other for so long that I wonder if we’re even able to love each other like that? Or does it just take awhile? — Is It Love?

There’s been some talk in the forum dating thread about the “slow burn” and how, if you’re someone who’s had relationships in the past that feel overwhelming in their specialness, it can be confusing to find yourself in a relationship that feels good but isn’t all fireworks and constant butterflies in the stomach. And there’s something to be said for those relationships that feel different than the ones that came before. The ones that came before ended eventually, right? Assuming you’re looking for one that won’t end, it’s worth exploring a different kind of relationship, one that feels unlike the ones before it.

But still, how do you know whether it feels different because it’s love or because it’s just friendship? A good way is to ask yourself how you’d feel if your relationship ended and you both started dating other people. Basically, how does the thought of losing him as your boyfriend feel? What if you could still have him in your life as a friend, but you weren’t intimate with each other and you didn’t spend as much time together? What if he told you today that it’s been great but he just doesn’t feel the spark he thinks he should feel with someone he’s building a relationship with? If none of these scenarios bother you, then it’s possible that what you feel for him is more of a friendship than anything else.

But here’s the thing: You don’t have to figure this out right away. It’s only been four months that you’ve been dating after seventeen years of being friends. It’s pretty natural that it might take a long time to feel the dynamic of your relationship shift. It’s also natural to want to speed that up. But if you’re enjoying your time together, try to resist the urge to label and define. Practice being in the moment, following your gut, and listening to your heart. Sometimes love is loud and comes on strong, and sometimes it starts as a whisper that you only hear when you ignore the other noise around you.

Recently, I started chatting with this guy whom I’ve known for three years. I’ve always had feelings for him, but he treated me like a little sister so I never pursued him. Fast forward to now: he’s graduated from the college that we both went to and has moved back to Florida; he says he likes me and he’ll be out here in California during Spring Break and wants to hang out. I don’t know how to ask if he only wants to hook up. I don’t want that. I’d want something more and I don’t want to sound like a crazy bitch asking “What are we?!” I’m no one’s casual fling. I deserve more than that, but I’m so nervous to ask what his intentions are. — What are we?

Ok, short answer: If he’s out of college and isn’t a school teacher and is using the phrase “spring break” to refer to a vacation that he takes in the months of March or April, then, yes, he’s probably looking to just hook up. Longer answer: If you don’t want a casual hook-up, don’t hook up with someone who is visiting for a few days from the other side of the country. Unless there have been conversations to the contrary — and there haven’t, and I agree you would sound crazy asking “what are we?” at this point — you have to assume that the intention is a casual hook-up. People don’t generally sleep with someone from the other side of the country while on “Spring Break” whom they intend to pursue a serious relationship with. Sure, these hook-ups can eventually lead to something more serious, and maybe he’s open to that, but that usually isn’t the motivation, you know?

So, what can you do? Well, be honest with him: Tell him you’re looking forward to seeing him but aren’t a casual hook-up kind of person and you wanted to make that clear before you see each other so there isn’t any weird ambiguity or awkwardness. Then the ball’s in his court. Now, on the chance that he does want to pursue “something more” with you, is that really what you want? With someone who lives in Florida? That’s really far from California. I’d do some soul-searching and make sure that your years of crushing on him aren’t fooling you into thinking that the something more you want is with him.


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If you have a relationship/dating question I can help answer, you can send me your letters at wendy​(AT)​dearwendy.com.


  1. Avatar photo juliecatharine says:

    WWS. LW1, not that this is the case with your relationship but when I started dating my husband it was honestly kinda boring at times. There weren’t fireworks or grand gestures (not that I expected them), just peaceful compatibility and damn good physical chemistry. Fast forward to now, married a bit over a year, and I grin and giggle to myself at least once a day about him and how stupid in love we are. Worst case scenario you guys are friends, take your time and see what unfolds.

  2. I’d run screaming if someone said they loved me after 4 months of dating.

    1. I would if they were a stranger (like, we met online or in a bar), but she’s known him for 17 years. I think it’s totally possible to fall in one- or two-sided love with a friend, even if you’ve never dated.

    2. Northern Star says:

      My now-husband told me he loved me after two months of dating. When you’re older and have some experience (or have observed others’ experiences), I think it’s easier to know what you want and feel like you’ve found it.

      Not in every case, of course.

      1. I knew on our third date. I smiled/laughed so much my face hurt. To be fair, we worked at the same company and I had an idea of what this guy was about. I also had on good authority how smart/kind/respected this guy was even though he could come across as a know it all.

        As Northern Star said, I also had a lot of experience dating and learning what I was not interested in.

  3. LW1 – Four months in I think it’s acceptable to say “I love you” if you feel it, but I also think it’s too soon to be alarmed if you haven’t heard it yet.

    LW2 – A guy who lives on the opposite side of the country who is coming in for a visit is almost surely not looking for anything serious with you. Also, from what you wrote, I can’t even be sure that he has any romantic interest in you whatsoever since it sounds like he has a trip planned notwithstanding your friendship.

  4. LW #1 —
    Very confusing letter. On the one hand you ask ‘will we ever be able to love each other like that?’ based (I guess) on neither of you saying ‘I love you’ in the only 4 months you’ve dated. On the other hand, you say you have felt like saying it more than once. So, apparently, you can love him like that. Is your real question whether he will ever love you like that? We can’t answer that. Four months is not a shockingly long time for him not to have said those words. As in almost all questions of relationship ambiguity, the answer is to ask him and to have the discussion of where each of you thinks the relationship is now and where each of you hopes/expect it is going.

    Looking back as someone a lot older than you, and one who felt he was in love after 4 months, let me say that I now don’t think you can really know whether or not you love each other until you get out of the honeymoon phase of your relationship and progress down the path from mutual lust and interest to a deeper understanding and appreciation of each other which becomes enduring love. It is all too easy to confuse the exciting beginning of a relationship as love, and it actually is a sort of love.

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