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#279: “Help, I’m in love with my best friend and I don’t know what to do.”

Fred Savage in The Princess Bride. "Is this a kissing book?"

“Is this a kissing book?”

Dear Captain Awkward,

I’m in love with my best friend. That sounds like a really lackluster problem, but it’s really starting to weigh on me in a way it never has before. I’ve tried to talk to some other friends about it, but they don’t really seem to count as outside opinions (our friends are basically gunning for us to get married). I would really appreciate an unbiased viewpoint!

My best friend is wonderful in every way. We’ve been inseparable since high school. Everything we do together just seems so special and memorable, like a movie. We can keep up with each other and encourage each other. We adventure together. We can talk to each other in a comfortable stream-of-consciousness and work out our problems together. We grew up together. It’s been five years and my heart still jumps up into my chest every time he walks through the door.

I’m so in love with him, but I’m starting to wonder if anything will ever change between us. If we ever started to date, physical intimacy would be the only new development; we’ve already covered most of the bases for beginning and sustaining a healthy relationship. I’ve reached a level of intimacy with him that I’ve never found with anyone else. Pursuing a relationship with him seems so strange to me. It’s something I thought about a lot when we were a bit younger, but now it just seems silly. I see us staying friends forever, and I could even picture us being married, but I could never see us in a relationship together. It’s just been too long- it almost seems like we’ve passed the mark. I just don’t see anything to be gained by dating each other.

I’m also constantly unsure of his feelings. He broke up with a serious girlfriend several years ago because he was in love with me, but I was dating someone and wanted to see it through. We spent some time talking about how we wanted things to be different last year, but we never went through with it.

I’m not sure what to do. I want to date other people, but he gets in the way of a lot. I took a year off from dating because I was finding it difficult to build healthy relationships and emotional attachments with other people; it always comes back to him.

I’m so confused and I don’t know what to do.

Thank You!

Tangled Up

Dear Tangled Up:

I’m pretty sure you already know what to do.

You have three options here.

1) Maintain the status quo, where you don’t say anything directly to your friend but bore the shit out of your other friends with your endless need to analyze and discuss how you *should* be a couple. (NOT RECOMMENDED).

2) Decide that you don’t actually want to be in a romantic relationship with him. Maybe if it was meant to happen it would have by now. Quietly do the necessary grieving, distracting-of-self, and getting over. Maintain the friendship. (TOTALLY POSSIBLE). 

3) Speak up about your feelings to the one person who can do something about them: Your dear, beloved, crushed-on friend. (SERIOUSLY CONSIDER).

I don’t really have an opinion on whether 2) is a better option than 3) or vice-versa. I do have an opinion that you should not skip directly to marriage with someone you “could never see yourself having a relationship” with, and it’s worth exploring the why of that a bit and being honest about your reservations.

I suspect this is partly a question of attraction (what Commander Logic calls “groin feelings” and what makes the kid in The Princess Bride ask if it’s “a kissing book.” ) Do you have groin feelings? Maybe spend a week or so…in your bunk…and think that through.

If you have groin feelings, I am going to suggest that you lead with those. Text or email friend and say “Friend, are you free tonight or tomorrow? Because I’m thinking maybe it’s time to make out with each other a little bit and see if this on-again, off-again crush we have on each other has legs. Would you be up for it?

Notice I did not say figure out every aspect of how your future relationship will work and whether the whole thing is a good idea. Nor did I suggest that you try to find out how he feels first so you can be sure you won’t be rejected. None of that fucking matters, you don’t have to figure it out this second. Do not construct a FEELINGSBOMB. You’ve got years of friendship to tell you that he’s a good person and you love his company, so figure out if his lips feel good on your lips. Is this a kissing book?

If he says no, laugh and say “Well, I had to ask!” Get ready for a few weeks of fleeting awkwardness followed by laughing about it and being fine. A friendship like the one you describe can definitely survive a little bit of awkward crushing. It survived the times he was into you, right?

We’ve said it here before: Nobody gets to the good parts of love without risking rejection and awkwardness. Rejection and awkwardness aren’t really that big a deal.

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42 comments
  1. Andie said:

    Good advice from the Captain as always,.. I’d go with option C, myself, especially in light of the fact that he has already admitted to romantic feelings for you.

    CA is right in that there is a chance for awkwardness. I did the FEELINGSBOMB thing with my best friend a few years back and in my case, I was turned down (twice actually.. wait for the feelingsbomb fallout to totally dissipate before drinking with said friend again, is all I’m saying). It was devastating at the time, and took a while for things to be normal again, admittedly. But we got back to that Normal-for-us place again and are both happy with the way things have turned out in the long run.

    I wish you much luck! Go git’ im!

  2. solecism said:

    I totally turned a might have been into a how about it situation. And we are still happily together 6 years later. We’d known each other since I was 15, and I’m now in my 40s. Our situation was different from yours in that I moved away and had done a lot of different things and we’d stayed in touch casually and infrequently during that decade. We’d both thought about it in the past, but the timing was off, much like your situation, with one or the other in a relationship. Finally, we were both free, and I took the plunge. And here we are.

    But zie might have said no. It is always a risk. If it’s a no, you can still be friends as long as you both respect the boundaries and get past the awkwardness. You have so much history together that it can weather this. Keep in mind that if it doesn’t work as a romantic relationship, at some point down the road, your closeness will likely fade. It’s hard to sustain a romantic relationship with someone who is more invested in a particular friend, no matter how platonic that friendship is. So at some point one or both of you will choose the relationship with sex over the emotionally intimate relationship, so that the former can develop into the most emotionally intimate relationship. But you don’t need to worry about that right now. It’s just a long-term consideration that is completely irrelevant to figuring out right now. Right now think about kisses and sexy times and whether that’s a possibility with this person in this moment.

    • Kaz said:

      So at some point one or both of you will choose the relationship with sex over the emotionally intimate relationship, so that the former can develop into the most emotionally intimate relationship.

      I actually strongly disagree with this. Yes, it’s the way it works for a lot of people but it’s not some universal constant or something to be passively resigned to if it’s not how you want things to go. If you want to keep a platonic relationship as most important in your life, that can be difficult and require a lot of communication (it’s pretty contrary to societal messages about how relationships Ought To Go, so it’s very easy for nasty assumptions to slip in if you don’t talk) but it’s not impossible and I hate that it’s so often made out to be.

      Sorry if I sound upset, but I’m not interested in romantic relationships and this kind of thinking is why I spent years thinking I was doomed to misery and loneliness.

      • Any reading recommendations blogwise? Romantic relationships do nothing for me, but I don’t know much material I can relate to.

      • solecism said:

        I did not mean to leave out asexuals/aromantics. It is absolutely possible to have a deeply fulfilling life with relationships that don’t entail sex and/or romance. I have at least one close friend in this situation. In that case, it is certainly reasonable that a platonic friendship is the most emotionally intimate connection. However, LW made it clear that zie is interested in some sort of sexual/romantic relationship, if not with best friend, then with someone.

        I am generalizing here, but I do tend to think that it is nigh impossible to have a successful, healthy, long-term committed monogamous sexual/romantic relationship, when that is not also the most emotionally intimate relationship. Being more intimate and committed to a platonic friend over a sexual partner will inevitably strain the sexual relationship, and I don’t see any good way for it to survive when the person in the middle is constantly pulled between two opposite magnetic poles. Now this need not apply to poly or open situations–the dynamics are so much more complex, and I have little direct or observational experience of these situations. And it does not really apply to asexual/aromantic folks.

        I am sorry that all of those omnipresent messages of “happily ever after” left you feeling like you were doomed for so many years because no alternatives seemed to be available. I happen to currently be in a committed, monogamous relationship and mostly happy. But I have also spend much of my adult life single and mostly happy. And I have been in a monogamous sexual relationship and been deeply unhappy and desperate. Being in a sexual relationship does not axiomatically mean success, nor does living without sex mean failure and misery.

        • rachel said:

          I feel like you’re making a *lot* of assumptions about a *lot* of people here.

          While you may not be able to (or want to!) have long term sexual/romantic monogamous relationships that aren’t the most emotionally intimate relationships in your life, I don’t think that has to be true for other people… I think it depends entirely on what the people in that relationship have decided that they want and what .

          It feels wrong (and prescriptive! And part of the happily-ever-after-fairytale-problem!) to say it CAN’T happen.

          I know a few people in secure, monogamous sexual/romantic long distance relationships that they have no intention of making short-distance in the next five years (if ever) and it strikes me as pretty odd that you don’t think it’s possible.

          And to be honest, I think that the idea that if you have a monogamous sexual partner, they have to be your most intimate relationship kind of sucks and contributes to the fairytale.

          • solecism said:

            While you may not be able to (or want to!) have long term sexual/romantic monogamous relationships that aren’t the most emotionally intimate relationships in your life, I don’t think that has to be true for other people

            Is this a personal “you” directed specifically at me? Or a more general conversational “you”? I agree that the sexual/romantic relationship doesn’t HAVE TO be the most emotionally intimate relationship, and every relationship gets to be defined by the people involved.

            I apologize for giving the wrong impression and setting up your hackles. Now I am going to ruin my apology by pointing out that I was trying very hard to not be prescriptive. Notice the qualifiers “I tend to think,” “nigh impossible,” ultimately, I am simply expressing my opinion and offering a prediction, based on my experiences and observations, not stating the Way Things Are For Everyone. I said nothing at all about long distance relationships. I am not sure where I gave this impression. I think they are very possible. My current relationship was long distance for 4 years before we were able to move in together.

            Nowhere do I say that the romantic/sexual relationship HAS TO BE the most intimate relationship. Is this often (possibly even mostly) true? I suspect yes. Because alternate situations are likely to involve more inherent stresses that require much more communication, honesty, and careful navigation to successfully maintain them. That’s hard enough when it’s just one person. Is it impossible to maintain an emotionally intimate relationship that’s closer than the sexual/romantic relationship? By no means. Anymore than poly relationships are impossible and doomed to failure, which I don’t believe. However, larger, more complicated, and more prone to failure? Sure. Individuals are complicated, juggling is hard, and the more intimacy balls you try to keep in the air, the harder it is to keep them all going. It takes, skill and practice.

  3. caius said:

    If only I had had these options clearly layed out when I had a similar situation.

    I took option B after letting the friend in question help rationalize that I did not have feelings for her (my first mistake). Then I did not let the Feelings Fallout vanish before drinking with said friend. When pants-things inevitably happened it strained both the friendship and my emotional state for long afterwards.

    Please make sure to take the appropriate emotional precautions no matter what option you choose. Taking some alone (or at least away from friend) time for necessary getting over is key to option B. Don’t make my mistake.

  4. DDog said:

    “Is this a kissing book?” is my new favorite pantsfeelings gut-check question!

    I would also add that as the Captain has said before, a noncommittal answer or silence from your friend in response to Option 3 may be your answer (“no thanks”). I’ve taken Option 3 before and gotten non-answers and at that point Option 2 or GTFO are your boundary-respecting courses of action. As much as it sucks to put yourself out there and get a meh instead of a clear yes or no, it sucks worse if you keep asking or revert to Option 1.

    It’s a joy to have such a strong, intimate friendship in your life. Perhaps your pants will get to hang out together without needing to change the existing structure of the relationship, if that’s how you both want to work it. Or not. You and he get to decide!

    • Cora said:

      I would also add that as the Captain has said before, a noncommittal answer or silence from your friend in response to Option 3 may be your answer (“no thanks”).

      Yes, yes!

      In a perfect world, everyone would be forthright, and people who weren’t interested would say a polite, clear ‘no’ every time. But in the real world, a lot of people, for a lot of different reasons, say, “uhh” or “maybe…? I guess…?” or “ummm” or “OH LOOK AT THE TIME” or “” instead. Which leads to all kinds of awkward on both sides. It is generally best for the mental health of all involved to treat anything but a “yes, definitely!” as a “no.”

      Not to mention: you deserve someone who responds to your interest with a “hell yes!” as opposed to an “um, I guess….”

      • Cora said:

        (That last “” was supposed to contain the word silence in angle brackets, because I forgot that HTML means that angle brackets are eaten. So pretend it says “*silence*”.)

        • Ethyl said:

          I actually did, no worries :)

  5. FlyBy said:

    I know of a guy and a girl who are best friends and tried option C, (in the form of post-break-up sex, which probably wasn’t the best choice) decided nah, this is like sleeping with a sibling, and are still best friends. I don’t know if/how long things were awkward after that, but they certainly were back to normal within a few months. So it’s possible.

    You mentioned not being able to see yourself ‘in a relationship’ with this guy. Keep in mind that ‘relationship’ covers a lot of ground. If the two of you get together, it may not look or feel like your other dating relationships, and that’s okay. You said “If we ever started to date, physical intimacy would be the only new development; we’ve already covered most of the bases for beginning and sustaining a healthy relationship.” That sounds pretty good to me.

    • Ethyl said:

      My best friend and I had an awkward moment in high school where I said “hey, how’s about it?” and he said “meh, nah.” It was awkward for a while, and our friendship has gone through this and other rough patches, and we are in our mid-30s and are still BFFs (the only person I consider closer is my Beloved). A friendship like the LW described can certainly weather this and much more.

  6. Esti said:

    LW, I wonder if some of your confusion over the situation is because non-romantic relationships are often devalued by the world at large. You can have friends that you keep your whole life, and who are really, really important to you, and who make you feel special and who encourage you and who “get” you. Those friendships are not any less valuable or real or important because they don’t involve your groins.

    I have definitely fallen into the trap of thinking that any male friend, if I think he is super awesome and want to do lots of stuff with him, must be someone I want to date because that’s what you do with someone you really like who is of the gender(s) you are attracted to. And it can be confusing, because if being with that person makes me feel awesome about myself (as good friendships should!), my brain sometimes gets all tangled up with whether I am feeling good or feeling them when I’m around them. But not all amazing friends are people you want to date. I have friends I absolutely adore but am just not attracted to, and I have friends I adore and think are cute but who I have no interest in dating (they refuse to wake up before noon! they have totally different life goals than me! we would kill each other if their extreme mess and my semi-tidyness tried to co-exist in the same living space!). But they are still the people I call when disaster strikes, and the people I share ridiculous inside jokes with, and the people I want to spend all night drinking beer with, and the people who encourage me and believe in me.

    Now, maybe you are attracted to this guy and do want to try dating him. If so, go forth and follow the Captain’s third path! But as you try to figure that out, ask yourself what kinds of things you do fantasize about doing with this guy. When you say you can see being married to him, do you mean that you can see the two of you cuddling on the couch and having sexytimes and kissing on a bridge in Venice? Or do you see the two of you calling each other when shit hits the fan, and helping each other make life decisions, and still adventuring together years in the future? The former isn’t the only thing you need in a romantic relationship, but for most people, it’s a thing they need. But if what you really want is just to stay close and help each other through life and have fun together, then you can have all of that without taking things to a romantic level. You don’t have to pants!love someone to love them.

    • +1 to this. Emotional intimacy – which it appears LW already has with this superfriend – and physical intimacy don’t have to go together! It’s totally possible to lovelove someone without wanting into their pants. Be honest with yourself about how you feel and what you want, and take Captain’s option B or C as appropriate.

  7. Sarah G. said:

    I fell in love with my best friend and finally screwed up the guts to tell him. He said, “wow, I’m really flattered! but not interested,” and that was that … for a week. Then he told me he was in love with me back and we started going out. It’s been about 13 years now and things are still going well.

    There’s a lot of really wonderful stuff that comes along with having a relationship with your best friend. But there’s one thing to think about. Do you have any other nearly-best-friends? Because if you date your best friend, eventually there will be a bump in the road and you will dearly want to talk to your best friend about it but, as it turns out, he (in his role of boyfriend) will *be* the bump in the road. This isn’t an insurmountable problem, but it is a vexing one. Make sure you have other close friends, too.

    • Bev said:

      I have this problem with the whole best/boy friend thing. While it means I have to talk through issues, not having a place to vent is frustrating.

    • aliaras said:

      This very situation made me closer to some friends. Especially when I got in a poly relationship with my boyfriend and the person I’d previously been flapping at when my boyfriend was the source of frustration.

  8. I just don’t see anything to be gained by dating each other.

    In combination with not a single word in the letter about any sexual feelings this led me to think that perhaps the LW doesn’t actually feel horny for her friend.

    • See it made me question what the LW considers “dating.” I think for some people dating is this thing where you go out to restaurants together, and have awkward conversations. And sometimes “Relationships” involve jumping through socially approved hoops in order to access the pants of the other person and then more hoops to living together and then more hoops to married. This may not be true of the LW but I’ve known a lot of people who consider “Dating” and “Relationships” to be something other than Best Friends + Pants Feelings.

      You may be right, but I think it would be good for the LW to try to analyze what she’s thinking about when she says a “Relationship.” I personally don’t understand her thought process when she says she can see them married, but not in a relationship? Newsflash, marriage is a relationship, just one with some fancy paper and jewelry. (Or what Flyby said earlier, but way nicer than I managed.)

      She’s right when she says “It’s just been too long- it almost seems like we’ve passed the mark.” They’ve gone well past the beginnings of a relationship where you date and get to know each other and everything is all heady and uncertain. Now they are a couple that has been together for 4 or 5 years, but has never had sex. Like it or not if they are best friends and are both not dating because of the other person (which is what it sounds like) they are IN a monogamous relationship, just without the pants benefits.

      If it were me, I would want to go about getting those additional pants related benefits as soon as possible.

      • I’m so sorry for assuming the LW was female. Just guessing based on the proposed legality of marriage between them. But I suppose you could be a gay person somewhere liberal.

      • Ethyl said:

        “Like it or not if they are best friends and are both not dating because of the other person (which is what it sounds like)…”

        That sounds like it to me, too…. Also, the LW also said that zie had tried to date but that the other person “got in the way.” This concerns me, because it makes it sound like the LW wants to date other people (and maybe find pantsfellings?), but this other person has attained such a place in LW’s life that there’s no room for anyone else. LW, I’m going to channel Sheelzebub and encourage you to ask yourself if this relationship — how it is right now, not how it is in your ideal future — if this relationship will still be making you happy in 5, or in 10 years? Will your friend freak out if someone else is more primary in your life? Will you freak out if he has someone else eventually? Good luck, LW, this sounds like you have a lot of thinking to do.

        • JenniferP said:

          Sheelzebub is the best “you’re probably not that into him!” person around ever, right?

          • Ethyl said:

            Oh totally!!!

  9. alphakitty said:

    If you go for option 3, I think the Captain’s advice about how to express it is great: when you’re past that initial text, take the relatively low-key approach of saying that you feel like the “what if?” has been hanging in the air for a while. You’ve felt the physical attraction, you’re pretty sure he’s felt it, but it’s never seemed like you were both feeling it (or feeling like it was a good time to take that risk) at the same time… and at this point you’d just like to KNOW: would that work between the two of you, or not?

    Because you feel like if it would, that would be pretty freakin’ awesome, because you could have your best friend and your sexyandromantic friend all in one. That on the other hand, if it wouldn’t, that wouldn’t be the end of the world, you’d just be like “nope, chemistry’s not there, that’s not meant to be a dimension of this friendship,” and you’d go back to your wonderful friendship, but at least you’d know. Because with the not knowing, you’ve caught yourself holding back with other guys, thinking that if you could have it all with him, that’s what you really want.

  10. xenu01 said:

    Here is where I might start:
    Think seriously about a possibility (however slim) in which you bring up lovefeelings and he says, “Oh no, LW, I don’t feel that way about you anymore.” Think about a possibility where things are a little bit awkward for a while and maybe you have to give each other space and then forever afterward there’s a little bit of a shy distance between you, or at least for a very long time and maybe years. Can you work with that? Can you live with it?

    If your answer is yes, I’d say go for it. My suspicion is that if you have had feelings for five years for him that it’s going to go the festering route if you don’t say anything to him. Meaning, you might whoopsdrunkFEELINGSBOMB or something else. So maybe it’s better to face the possibility that he says no, because maybe he will say yes, and either way, once you’ve popped the zit (sorry, gross) you can start healing, or adjust to the New World Order.

  11. Yan said:

    Scenario 3 — I love the script AND its corresponding notion of figuring out now (just now) what might be possible. Gather the facts, if you will, and see if you want to gather more.

  12. tessellation said:

    I did C. Platonic friend and I had been close for many years and eventually the option for more became available. I figured if there was mutual attraction, it ought to be very easy to stir up. Here’s how I did it:

    – He expressed an offhand desire for a particular wine.
    – I got a bottle a week later and told him I had it. He invited me over, made dinner, we opened it and watched a movie.
    – While sitting on his couch, giggly on wine, I moved closer and leaned my head on his shoulder. He put his arm around me.
    – We watched a few more movies semi-cuddling like this before we agreed it was very late and we were tired and driving wasn’t a good idea (which was an excuse because the wine had most likely worn off). We laid down together for a nap. All was wholesome and aboveboard, but when we mutually threaded our fingers together and clasped hands it was obvious we had broken the platonic friend barrier. Holding hands can be really intimate.
    – Then, hours of exploratory touching and awesome makeout and some talking about how long we’d liked the other and some napping. Mostly makeout, though.

    We had very little physical contact as friends (didn’t even hug much) so the mutual couch cuddling was a crystal clear “I LIKE YOU THIS WAY” sign for us. The way our physical interactions ramped up gradually was very low pressure and unmistakable. I never got mixed signals or weirdness. I trusted my friends’ reactions to be honest and I trusted that whatever happened wouldn’t wreck our friendship. If he hadn’t responded in kind, I would have backed off and it would be no big deal because I genuinely liked our friendship as it was.

    As the LW articulates, there is a strange twilight zone between “close friend” and “romantic partner”. It can be a weird transition. It’s been four months and I think we just recently got comfortable with the idea of the other as our romantic partner. It’s the same solid friendship, but we get naked together whenever possible, and we are more invested in the other’s ups and downs, which we talk about (ideally when naked, because goddamn it’s awesome).

    I think that the fact that the LW is unsure of friend’s feelings – or that friend is acting wishy washy – is a bad sign. Maybe the potential is there but the timing isn’t right. I do think LW should be brave and honest and try option C, because even a negative outcome will set them free to ask for a break from the friendship (option B). Option B could be a very healthy thing for the LW and the friendship, but they really need the clarity that will come from option C first.

    • aliaras said:

      This is pretty much *exactly* how me and my current boyfriend got together. We had this thing we called “beers and battlestars”, in which he was introducing me to good beer and Battlestar Galactica. The first night we did this, I took the excuse of two beers over three hours and 3:30 am to stretch and declare, “I’m falling sideways on you now.” I waited, counted to three slowly in my head (to give him the opportunity to go “noooooooo” and prop me up, or some other method of saying no while keeping the atmosphere light), and then cuddled on him.

      This kept happening for ~a week or two. I think we watched an entire season in that time? It was very much an excuse for physical contact. After one particularly late night at my place, I said he was welcome to go to bed at home or right here if he wanted. We slept together perfectly platonically for another week before it turned into no-pants-time. And man, that was a good time when it happened.

    • PomperaFirpa said:

      Oh my God, I DID THAT. Only it involved a bottle (or two) of wine, Raiders of the Lost Ark, cuddling, and me getting completely loopy and asking, “So, weird question, we haven’t tried kissing each other yet, what are your feelings on that?” and he was all “I am so down with this idea, you have no clue” and it became a kissing book very quickly after that. A little over two years later, we were married; a little less than six years later, we had a kid. SO FAR SO GOOD.

      On the other hand, I have also done that waaaaay in the past with a best friend who, it turned out, was gay and very much in the closet and not into me in a groiny way! That one did not go as planned from my part, and was really awkward for a while, but we are still awesome friends and all is well.

      What I am saying is: LW, GO FOR IT. NO HARM NO FOUL IF THE ANSWER IS “NO”. It is scary as hell, but if you are willing to totally accept a “no” (instead of “and now I will pine for you forever”, which is not conducive to future friendship status), then you lose nothing* and possibly gain a friend.

      * Okay, you do get to lose the “eeeeee I have SECRET CRUSH FEELINGS oh the butterflies! oh the romance! oh the twitterpatedness!” and spend some time in “aaaaaaaugh everything sucks” land, and that part is no fun, I will grant you. But I have some experience in this area, and let me tell you, if having unrequited crushes is something you enjoy (some do! I did!), you will find another one just fine, and this one will fade into the background. If you value your friendship more than the fun of having a secret crush, then you will do just fine.

      • Karen said:

        I don’t know any of you but reading these stories just make me so damned cheerful.

  13. Liennae said:

    Do option C. Do it before he ends up in another relationship and you’re stuck asking yourself “What if?” until the day he pops the question to her. Do not become the protagonist of “My Best Friend’s Wedding”.

    Saying that “If it was meant to be it would’ve happened by now” is true in some cases, but don’t let it be an excuse to not take any risks. While I don’t advocate randomly sticking your tongue down his throat, I think the best way to find out if you have pants feelings for someone is to try kissing them (with their consent of course!). Otherwise it’s all hypothetical.

    Because I love giving personal examples, I shall share my story with you all. Yes, it IS a kissing book. Two (and a half!) years ago I was crushing on two of my guy friends, and I wasn’t sure which one I should pursue if either of them at all. I’m not the best at picturing sexytimes with guys I haven’t had sex with(for some reason it makes me feel like I’m doing something without their consent). It seemed like an interesting proposal for either of them, but not the decision maker I’d hoped it’d be. Life being what it is, I ended up kissing both of them within a few days of the other. One was awkward and icky, the other was passionate and soulful and and and(sorry I’m getting distracted now…) And I ended up dating the one that I loved kissing, and two years later we’re still crazy about each other.

    While not everyone I’ve enjoyed kissing has led to a long lasting and meaningful relationship, but it’s a great way to ferret out your true (at the moment) feelings. Sometimes trying to figure out your head and your heart is so confusing you stop seeing straight – but even if I didn’t see it at the time, usually the ‘tone’ of a kiss has said a lot about how serious my feelings (and pants feelings!) actually were for that person.

    If you let him know about your interest in a way that is not FEELINGSBOMB-y it should be easy to weather the awkwardness if he says no. (I like the Captain’s script for this!)

    However – if you’re already thinking “Yuck” to a kiss before it even happens, that is probably all the answer you need.

    I also think that you’re being a bit quick to dismiss the possibility of your feelings getting any deeper for this guy. Sexytimes and romance can bring things to a whole new level, especially when it’s with someone you care about already.

    I hope things work out for you, even if it’s just by getting the closure you need to move on to other relationships!

    • Do option C. Do it before he ends up in another relationship and you’re stuck asking yourself “What if?” until the day he pops the question to her. Do not become the protagonist of “My Best Friend’s Wedding”.

      Definitely do it before he asks your help in picking out the ring because you’ve become good friends with her, too.

      (And before you, like me, wind up witness to their proposal on your own birthday.)

      • liyyspoon said:

        Oh, *ouch*

        This the two-letters guys? :(

  14. DO IT. ASK HIM OUT.

    I once had a crush on my best male friend. I put off telling him for years. Even though I didn’t want to date anyone else. Even though I could easily imagine us married. At some point, the friendship started to feel like I was being unfair to him. I was coming to every interaction with a set of expectations/hopes/dreams that he was not aware of. It was dishonest of me, and I needed to set things straight. Yes, I could have made the friendship awkward by telling him about my feelings–but at that point, it was awkward for me to keep pretending to be just his friend.

    So I told him.
    “I need to tell you something.”
    “What’s up?”
    “I’ve had a pretty big crush on you for a while now, and I’m not sure what to do about it.”

    I had spent a long time imagining us together romantically, but actually dating each other was better, more exciting, and more satisfying than anything I had hoped. There was so much more to learn about each other than we ever would have as friends. You really don’t know what it will be like to date this person until you date him.

    Dating for almost three years. Getting married next summer. None of this would have happened if I hadn’t put my big-girl pants on and told him how I felt. You can, too!

  15. Red Shift said:

    I was on the receiving end of this relationship many years ago. Unfortunately for me, I was not attracted to my wonderful best friend (man my life would have been so much easier if I was, he is such a lovely and wonderful human being! He was also very attractive, I never understood the lack of “groin” feelings on my end). When he approached me and was honest about his feelings, I told him no. It was awkward for a few weeks, but our friendship was too important to both of us. We survived and continue to be closer than we ever were before (this happened almost 12 years ago!). In fact, my family (including my now husband) has pretty much adopted him as a brother, and he is considered part of our family now. In fact, he may be joining us for the holidays this year :).

    Don’t be afraid to ask. You will never know if you don’t ask. If he says no, then your friendship is hopefully strong enough to weather through, but at least you will know!

  16. Jiggs said:

    I want an update on this SO BAD.

  17. liyyspoon said:

    I am also Team Option #3.

    I am also still dating my long-ago superspecialbestboyfriend. We became BFF’s when I moved in next door to him when I was 15 (I know, sometimes I wanna barf on myself) and made the transion to groinfriends about 5 years later.

    What helped me re-frame the weirdness of ‘weird! Now he’s touching my butt!’ was the way I changed how I thought about our friendship (well, that and the fact there had been the occasional snog throughout the years).

    Namely, the fact there had been attraction between us, that I’d thought sexual-flavoured thoughts about him, had romantic feelings on and off (as you describe also, at least from his perspective) meant he was *never really my friend*. I had loads of opposite-gender friends who I never had such thoughts about, and so rather than us changing the friendship into something else, we were just dropping the pretense that it was a friendship at all.

    I hope this helps. Good luck!

  18. aliaras said:

    LW, I can also chime in to “option 3 not leading to pants time does not end the friendship”. I had a friend who I’d been flirting with the previous year. I had a crush on her, there had been a little bit of kissing, etc etc. So I got my stuff together and asked her if she wanted to date. She was like “uh…I don’t really see what would be different if we were dating,” and I was like “we could make out more? Cause it’s uh…fun?” and she explained that she wasn’t interested. MAJOR AWKWARD for that evening. But I went home and was a little bit sad, mourned the relationship that was-not-to-be, and we’re still friends today. And, with that resolved, I was able to get together with my totally awesome boyfriend when that came up in a couple months.

  19. irishup said:

    LW, I have been in your position more than once. You see, I hail from planet Easily Develop Pants Feelings. I also have several bfs who are the gender for which I develop Pants Feelings. Alas, I am HIGHLY susceptible to developing Crush Story Syndrome. I’m capable of just enjoying a crush; crushes are fun while they last, but eventually dissipate. But CSS is where the Relationship in Your Head has more emotional reality for you than the Facts On The Ground do.

    This phrase “I want to date other people, but he gets in the way of a lot. I took a year off from dating because I was finding it difficult to build healthy relationships and emotional attachments with other people; it always comes back to him.” makes me think that CSS is a possibility in this case. One of the hallmarks of CSS is how it interferes with IRL experiences, since Relationship in Your Head has so many rainbows and sparkly flying unicorns.

    Meta-analysis has shown that FEELINGSBOMBS are absolutely CONTRAINDICATED when CSS develops in the setting of BFs. Moderate doses of Reality, have proven highly effective in all but the most serious infections. As long as there is no Reality antidote, Crush Story Syndrome often remains fulminant and active. Granted, curing CSS is sometimes painful and awkward. However, with careful attention, CSS can remain in full remission, allowing a normal and active lifestyle and friendship to resume.

    Reality comes in several forms, and it may take a mixture of applications to result in successful treatment:

    – Interrupting CSS thoughts with actual memories of times Crush Object has pissed you right fucking off or bad habits Crush Object has that maybe would not be so wonderful to have around all the time. The idea is to interrupt perseveration on CSS thinking, which often has the effect of impairing judgment and can lead to FEELINGSBOMBS, boring your friends, and saying no to what could be better opportunities.
    – It may be mundane, but the old Pros and Cons lists can help. CSS causes inordinate focus and over-valuation of one side of the equation. Put some effort in developing the OTHER list fully, and really ask yourself whether these things work for you or not.
    – Using Your Words with Crush Object can result in conversations that reduce Pants Feelings, or make clear that BF is not quite right for you, or that you would NOT make BF happy. This can be AWFULLY painful, but remember, this is a best friend, who you want happiness for. If bf told you about someone who was NOT you, who wouldn’t or doesn’t make them happy, you would support them in not/no longer dating that person, right?
    – A formal date and/or some smooching often evaporates the conditions (sparkly unicorns, Pants Feelings, whatever) that precipitated the CSS.

    I wish you the best of luck, and that however it breaks, it’s mutual and your friendship stays strong!

  20. kamianya said:

    I know I’m pretty late to the party, but I just want to chime in as someone who’s been in a similar option, took choice 3, and it didn’t work out, since most of the replies have been “and now we’re dating.”
    I crushed on my best friend in college for a long time, and finally got up the courage to tell him. He turned me down (very gently). Our friendship didn’t suffer though, and in fact, getting that “nothing will come of it” helped me turn off the crush and get back to normal. I don’t know if that would have been possible without speaking up.
    So basically, I agree with the Captain for someone in this situation. Either you’ll end up with a significant other, or you may just get that impetus you need to finally move past it.

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