Tag Archives: crushes

Hi Captain,

I’m a twenty something female working in a retail job where it’s NECESSARY to work as a team. In the six months I’ve been at my job, I’ve built especially great rapport with a few people. The man henceforth named Paul is one of them. Paul is a year younger than me. Most of our dynamic has been sarcastic banter, punctuated by some more serious conversations about a wide variety of topics. After about two months Paul asked some questions about my opinions on romance related topics (we were off the clock and out in a group with coworkers), and I answered in the context of the happy/trusting/loving relationship I have with my boyfriend of 4 years. Paul seemed surprised to hear about him.

I later brought up one of Paul’s questions I didn’t feel I answered well, and he got extremely flustered and changed the topic. A week later he told me that he struggled with feelings for a coworker at an old job for a year or so before he really stopped having feelings for her, and he regrets that it took him that long to deal with an unrequited crush. Since he told me about that, he hasn’t brought up anything even remotely related to romance.

I’m pretty damn sure that Paul has a crush on me. He hasn’t said or done anything inappropriate either in or outside the workplace, and since describing that old crush has not brought up romance in any context (that was nearly 3 months ago). It doesn’t get in the way of our work, most of the time we still execute the sarcastic banter/serious topics conversations without a hitch.

But I definitely feel like there’s a weird feelings stalemate. In my personal life I would have confronted him about it long ago and let him know that if he can’t handle being around me, then he shouldn’t be around me, and I’d be happy to have his friendship whenever it’s just friendship. But given that we work together that’s not an option, and I don’t know what’s appropriate. I feel bad because I get the sense that he’s doing everything he can to keep the feelings off my radar since that story. If he were creepy I’d tell a manager, and if the fact that we get along didn’t make our job way easier and more enjoyable it would be an unwelcome but simple task to freeze him out. Ultimately I just want to be able to work and occasionally hang out with this guy in group settings without the sense that he’s experiencing heartwrenching crush feels half the time I laugh at his jokes. Is there even anything to do, Captain?

-Midshipman Awkward Sauce

Dear Midshipman!


You’re an empathetic person, so you are putting yourself in his shoes and wanting to make things better, but you can’t fix this for him. Short answer: Say nothing, it will get better soon. “Paul” is actually handling all of this very well, in my opinion, and it would be a mistake to stage-manage his feelings or pry further into them.

He most likely did have a crush on you, he figured out that it would not be requited, and he bailed out just in time before telling you about it beyond an oblique reference to a past situation. Of course he feels awkward, he’s got all these feelings and he can see how very close he came to 1) asking out a coworker and 2) macking on someone who he knows is happily coupled up. I think it speaks to him being a good person that he pulled back when he did. You can help everything get less awkward by being your same basic amount of work-friendly to him and letting him save face. In my opinion, he won’t thank you for addressing it directly: Imagine someone else peeling off a scab that’s on your body, and that’s pretty much what it will feel like for him if you bring it up before he does.

For now, return the text of your interactions to normal relations, ignore all subtext unless it does get angry or creepy or unless he sheepishly confesses, “I was developing a crush on you and that’s why I’ve been acting kinda weird lately” at which point you say “Aw,  knew *something* was up, but I didn’t want to make you more uncomfortable. So you know, I really like working with you and I’d like us to be friends, and I’ll follow your lead on that.” 

A warning sign: Danger Crush Points with a graphic of a hand getting crushed. Dear Captain Awkward,

I would like to ask for your opinion of a situation that is currently happening in my life, hopefully whatever you may say might give me another perspective.

I have a crush on the most gorgeous boy, my family friend and we’ve always been friends. He had a crush on me once, years ago, but now the tables have turned and it’s me who has these feelings. I just adore him, it’s the same old story.

There’s this other girl, one of the popular girls and she has a boyfriend who goes to another school but that doesn’t stop her and said boy from flirting all the time. She’s just all over him all the time and he is too, but all of my friends say that they’re just good friends and that’s it.

I just want to know, from the outside, without knowing all of the
information it may seem like he likes her, and I feel that way also, but I
swear sometimes he steals glances at me, we laugh and joke together
sometimes, he like obnoxiously sings songs to me in class to make me laugh (and he succeeds) and he’s shy around me, even though he’s one of the popular boys and he’s seemingly cocky and confident all the time. 

He’s so much different around his friends and it’s in those moments when we’re together at each others houses that I feel like maybe something could happen. These feelings I have for him, I just feel it in my stomach and in my heart. I want him so badly it hurts.

Captain Awkward, do you think anything could ever happen between us?

Because I would really like to know, so I could know if all this wanting
is for nothing. All I want is something…..anything.

Love, Eleanor x

Dear Eleanor x,

There is only one person who knows the answer to this question.

That person might like the other girl.

He might like flirting with the other girl but also like you (or someone else).

He might just like flirting with everyone and not like anyone in particular. Or, it may not have occurred to him that you might like him so he doesn’t quite see you that way. Attention from cool people feels good, there’s nothing wrong with him enjoying it.

Watching him like a hawk, reading all of his laughs and smiles and glances like tea leaves, and speculating on his desires are not going to get you closer to figuring out his feelings, but they are going to get you more invested in an outcome that may or may not happen. Trust me, you can spend years in this headspace, ignoring all other people who might be cool romantic partners, obsessing over the slightest changes in his facial expression, boring your friends with another analysis of “the way he leans” and yet getting no closer to putting your lips in the neighborhood of his lips.

What would happen if the next time he was at your house, without his friends, you said something like “I am developing a crush on you, is that weird?” or “Do you still ever think about us getting together?” and then you talked about it?

One possibility is always that he says, “I’m sorry, I don’t feel the same way.” Which would be embarrassing in the moment, but then you’d at least know what’s going on. You could take a little time to regroup and then go back to being friends. Your friendship survived his crush on you, why wouldn’t it survive this? Reminder, when someone tells you that, it’s best to say “Well, that’s sad news, but I had to ask” and then back off.

There are other possibilities, though. “Let me think about it!” “REALLY ME TOO ❤ ❤ ❤ ❤ <3”

I want you to think of everyone you know who is happily, mutually in love with another human. Your friends. Your family. Then think about everyone in the whole world who is in love that way. Every single one of us had to navigate an awkward moment like this. Someone had to be brave and say the thing. There might have been hints and signals leading up to that moment, but no one was ever sure before they took the leap.

Hope and courage and love, Miss Eleanor.

"You know that tingly feeling you get when you like someone? That's common sense leaving your body."

Hello Captain,

This seems like such an common problem that I was surprised there hasn’t been a post about it before – but then, maybe it’s so commonplace and everyone but me handles it fine so it doesn’t need a post.

Your column has helped change from a “build the crush up in my head” Firther to someone who Uses My Words and asks people out when I first become interested in them. Sometimes they say yes! Other times they say no but I’m still better off than I would have been had I let the crush fester! I can’t thank you enough for your advice on this topic over the years.

Yet now I have a problem. Over the past few months, I’ve developed a crush on this fellow, whom we’ll call Fellow. Fellow is in a serious, monogamous relationship and has been for several years. From my outside perspective, they are very happy together and likely to get married. I have no desire to negatively impact this relationship.

Fellow and I have been acquaintances for years, but have recently started talking more and have become Actual Friends within the past few months. We talk online quite a bit. We don’t see each other in person often but we got to hang out at a nerd event this weekend. Apparently, our in-person interaction is obviously flirtatious enough that several people asked me what the heck is going on with us.

I think he may be flirting with me with the assumption that it’s all in good fun and nothing will come of it. I’m worried that it’s dishonest and wrong to continue as we have been with him not knowing that I’m seriously interested and would make a move if things were different.

Fellow is also semi-famous in our particular nerd world, and has said things that imply to me that he perceives my sometimes-nervousness around him simply as being starstruck (not in an egotistical way; he always reminds me that he’s not a big deal and that we really are friends). It also follows that he may know that I have a crush on him, but think it’s more of a celebrity crush than real feelings.

I can’t tell him that I like him, right? No good can come of it.

Am I obligated to cut down on the flirting, or can I pretend it’s just for fun since that’s probably why he flirts with me?

And what on earth can I do to stop this crush from taking over my brain if I can’t talk to him about it?

I Was Doing So Well

Dear Doing So Well:

Having a crush on a monogamously attached person isn’t wrong (or if it is, I am retroactively sorry, like, 1,000 times).

Your instincts are also good on the whole “don’t tell the happily partnered friend about your crush because you don’t want to throw a wrench into his works or beach yourself on the rocky shoals of his disinterest” thing.

But your question illustrates the limitations of that strategy, when your endgame isn’t “get with this dude,” it’s “enjoy his company without shredding your own heart” as he casually flirts with you.

So this is about finding a way to take care of yourself. One way is to wait for the next time he flirts with you and address it.

Hey, it can be really fun to flirt with you, but could you chill out with it for a while?

He’s gonna say something like “Aw man, why?

And you can say “Eh, it’s just a bit too much, thanks” and leave it there. You don’t have to give reasons. Repeat versions  and variations of “It’s too much.“I know you don’t mean anything by it, but it feels like too much.” 

I’m usually against invoking Mysterious Other People Who Agree With Me That You Are Doing Things Wrong in discussions, but the fact that it’s noticeable enough in public that other people are commenting on it can be part of the reason. “In public it attracts more attention than I’m comfortable with, and in private it just feels confusing and inappropriate.

Get ready for him to defend his honor and your honor. But we’re just friends! I don’t mean anything by it! My girlfriend is okay with it! You’re my friend, you’re not some fangirl groupie, etc., etc.

The thing is, this doesn’t have to be about his relationship, the rules of his relationship, his just-a-friendly feelings for you, or whatever. This is about you and your comfort. His right to flirt with you ends at your comfort with that. You get to reset the boundary within your friendship. “No flirting for a while” is a perfectly reasonable request, and a true friend (especially someone with a little fame who is used to ‘starstruck’ fans) has a lot of room to be cool and understanding. You’re not obligated to keep flirting with him just so that your friendship will never change and he will always feel 100% okay about his behavior, so don’t get sucked into that trap.

This discussion might spiral into a FEELINGSTALK, if you set a boundary about behavior and he keeps digging for reasons.“I don’t want to get between you and girlfriend, or make our friendship weird, but the flirting stuff makes my feelings confused. The problem isn’t that I don’t enjoy it, it’s that I *really* enjoy it, in a way that feels inappropriate given that we are not involved and you are very happily involved with someone else. I’d like very much to stay friends with you, but I need the flirting to stop for that to comfortably happen.

In the screenplay in my head he says “Oh.” and you say “Bet you wish you’d just stopped back when I said ‘can you lay off the flirting for a while?‘”

The other way is to pull back a bit from the friendship and put your energy into meeting new people and otherwise distracting yourself. You don’t have to slow fade or cut things off, and you don’t have to notify him that you are doing it or why. Just let him do the work of initiating conversation for a while. Maybe train yourself out of responding immediately by filtering his emails to a folder that you check once a week. Maybe don’t be so available on IM. Maybe be more scheduled about IM sessions or phone calls so that you can compartmentalize a bit and it’s not all flirty messaging, all the time. When you have a crush like the way you have a crush, your brain interprets any attention from him as “Happy Reward Times! RELEASE THE PLEASURE CHEMICALS” and you need to cut into that cycle somehow.

If he notices that you are not so available and asks you about it, and if you feel up to it, you can level with him. “Since you ask, last time I saw you at Event, we were very flirty, and it made my feelings confused. I don’t want a little crush on you to make our friendship weird or lead to anything inappropriate, so I’ve been pulling back a bit until my feelings get less awkward. I’ll see you/talk to you in (time frame that is probably a few months), is that cool?

Everything that makes you fun to flirt with for this person is within you. It’s not some glow imparted by this one dude’s Nerdfame or attention, it’s your wit and attractiveness and good humor and loyal friendship or whatever Terrifyingly Amazing stuff you’ve got going on. This is the good part of crushes, the part that lights you up and makes you smile and get great haircuts on the regular and stand up straight and flirt shamelessly with hot nerd celebrities. Keep being brave and awkward, and when love comes to you it will come correct.


I am heading to Texas for the first time ever tomorrow morning, to hang out with my sweetheart’s family & friends. January is a good time to get the hell out of Chicago for a few days, yes? So I won’t be posting regularly for about the next week.

In the meantime, per someone’s request in one of the many recent threads, this is an open thread about crushes and the concept of Limerence. Have you ever had a crush that just felt unshakeable and like it was making you stupid? What cured you?

True story: Over a decade ago I had a longstanding crush on a very close friend. We were one of those inseparable pairs. We worked together, did everything together, people constantly mistook us for a couple. Despite ZERO sexual chemistry, I drank the “What a good couple we would make! We already do everything together!” Kool Aid and decided we should be soul mates. In my defense, it was Washington D.C. in the 1990s. If you’ve ever watched the West Wing, you’ll have an idea of what the dating pool was like: Deeply unsexy workaholics who never stop talking. I know those characters have an avid fannish following, which, okay, cool if that’s your thing, I guess? The whole “I am convinced everything I say is vitally, deeply important and you should listen while I speak in paragraphs” thing really doesn’t wear well on 25-year-olds fresh out of the intern pool. I found one chill, not-ugly dude who had interesting things to say in his paragraphs and seemed interested in my paragraphs to the point of eating lunch with me every day and hanging out with me both days of every weekend (and eventually living 2 doors down in the same building); I was going to hold onto him for dear fucking life.

My strategy for making this shit happen was vast and complex. It included:

  • Dramatic sighs.
  • Dropping hints and badly timed sexual jokes that were not answered in kind or received with anything but patient forbearance or kindly pretending that whatever I had just said hadn’t really just happened.
  • Long meaningful glances….that seriously made him ask one time if I had something wrong with my eyes because I was not blinking sufficiently to lubricate them.
  • Having long, involved discussions with all mutual friends about the depth of my feelings and how this person and I should obviously be together over the course of years, plural. How my friends did not euthanize me and feed me to the animals in the Woodley Park Zoo, I will never know.
  • Getting interested in things I had no actual interest in for the sake of spending EVEN MORE TIME together. Like, going to mass with him every week. In Spanish. A faith that I had long ago abandoned and language I do not understand or speak.
  • Trying to turn our hangouts into stealth dates by taking him to dimly lit romantic places, where you recline on cushions and eat while watching belly dancers and then watching him like a hawk to see if he had reactions to the sexy belly dancers that might possibly be transferred to me. NOT AWKWARD AT ALL.
  • Totally ignoring the prospect or possibility that anyone existed, because this was obviously the person I was meant to be with and I was going to prove that I was the most loyal and patient person in the world and will this into being!

One day, after years, plural, I could not handle my feelings in silence (by which I mean painfully obvious “conveying” and hinting and also talking about them at length to everyone but him), so I wrote all of them down in a very long letter on good stationery. Then I recopied the entire thing so the handwriting would be nicer and there would be fewer ellipses.

You’ve read my blog posts, right? Imagine the FEELINGSMAILS I am capable of generating. Comprehensive, funny, heartfelt, sexy, and above all supremely logical cases for why you and I should be together, In My Pants, Love Always, Me.

Instead of sensibly setting this letter on fire, I put it in an envelope, walked to his house, hung out with his roommate for a bit, excused myself to go to the bathroom, snuck into his bedroom, and left the note on his pillow.

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Dear Captain Awkward:

I told my crush that I like him and he said he wouldn’t tell anyone and he told people. Now everybody knows. What should I do?

Red Head

Dear Red Head:

Every single person that that guy told has had a crush on someone themselves, so hopefully they’ll be cool and not judge or try to embarrass you about it.

You might get some gentle teasing or people bringing it up. If that happens, I suggest you pause for a second, roll your eyes, and say “Correction. I did have a crush.”  Practice saying it in the mirror or with a friend so you won’t get flustered.

You were brave and cool for telling your crush about your feelings, and everyone here is secretly giving you an awkward high five. You couldn’t have predicted he’d act like a big jerk who would use your sincerely expressed feelings to feed his ego, and you didn’t do anything to be embarrassed about. Even if he didn’t share your feelings, the right thing to do in that scenario is to say “I wish I felt the same, but I am very flattered and glad you told me. Of course I won’t tell anyone.” And then duh, don’t tell anyone.

Keep being awesome and awkward.

Count Rugen from The Princess Bride looking saturnine.

We are men of action, and lies like “It just happened!” do not become us.

Dear Team Awwkard,

Ok so here it is: I’m back at university after having to take time out due to depression and a very bad reaction to meds last year. I have a feeling that the depression was in a large part due to the relationship I was in at the time where my partner had Major Depression and Other Issues which meant I spent a lot of time trying to manage his crises, get him to seek help etc and deal with the emotional abuse that he threw at me when he had an ‘episode’. That relationship ended in February and I am much happier now, breaking up with him was a bit like stopping banging my head against a wall. I made the decision that since this is my last year of university and I am going to be thinking about jobs/a career/relocating that a serious relationship isn’t something I am looking for, because I want my decisions to be focused on what I want.  My family have been wonderful and supportive throughout everything and I am happy to be back at university although I still worry about things like work habits and slipping back into how I was behaving this time last year.

Over the summer I got a job at a pub to try to pay off my overdraft and met J. J, who has a girlfriend, worked in the kitchen and as most of the staff who worked at the pub tended to socialise after work together, we became friends, then good friends. He has just started university and I went to visit him during his freshers week because we enjoy going out together and he is fun to hang out with. Well the first night he explained that him and his girlfriend had decided that they were allowed to sleep with other people that they thought might be good relationship material. Their relationship is iffy, something I see as a combination of going off to university, the two year itch and probably other factors as well although we don’t tend to discuss it very often. Long story short, we wound up getting drunk that night and having sex. Very good sex. That happened again the next night and the morning after too.

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Dear Captain Awkward,

Three years ago, I skipped 8th grade and started high school.  Most people were awful about it, but several girls and one guy (ONE! In my WHOLE GRADE!) who actually spoke to me treated me like a was a human being with thoughts and feelings, because I AM.  Being sad, lonely, and scared, I became close to these people, and quickly developed a crush on That One Guy.

Everyone has a That One Guy (or Girl), who makes them feel happy and giddy and better on a crappy day, at some (or many) point(s) in their life.  Unfortunately, my current That One Guy has solidly Friend-zoned me.  He is kind and smart and athletic and funny and, while he’s not gorgeous, his personality makes him seem to me much more attractive than average, which is likely how a stranger would see him.  Yet he is COMPLETELY oblivious to my feelings.  Once, he asked a friend of mine (who didn’t know about my feelings for him) to Junior Prom IN FRONT OF ME, then got confused when the next day I said I probably wasn’t going.  That’s how oblivious he is.

Anyway, I have recently decided I need to get over Mr. Oblivious, because he is now dating someone. (Another sort-of friend with no idea about my feelings. YAY!)  I was literally attacked by the thing sitting on top of my Facebook Newsfeed telling me that they are now in a relationship.  I need to get over him.  It is not healthy to have feelings for this guy anymore, because at this point if he ever did ask me out, we’d be starting at such unequal levels of FEELINGS that it would have disastrous results and, more to the point, he is Not Interested, which makes him Not Worth It.

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 Dear Captain Awkward:

I’m a 25-year-old male with a girlfriend of a little over two years. We’ve had our ups and downs over time, but for my recent memory, which probably means the last year, things have been going well. We have a lot of fun together, usually on our own as most of our friends have moved away as they get real people jobs. She is supportive, caring, funny, we have good communication in most areas (caveat upcoming!) and is someone I can see myself being with for a long, long time. The only negatives with our relationship before last week were 1) we have issues that have prevented us from having sex for our entire relationship, 2) she can become obnoxious when she drinks, and she drinks semi-frequently, and 3) she has a far shorter attention and tolerance span than I do. That hasn’t been much of an issue historically, but lately I have been reading up on feminist stories and consuming a lot more information, and it’s just not something we can share in doing because she isn’t that interested in it while I am bordering on obsessive.

     These three problems have seen little flare-ups throughout our relationship where they become more than just a thought regarding our future and become actual issues, but we’ve worked through them at the time and they never really resolve, just slide back to low heat. I have been focused on her for our two years and building a relationship with her.  I’ve never had a problem liking someone else or thinking about another woman in any romantic way. She’s been my only long-term girlfriend, and occasionally I’ll feel like I missed out because of my lack of past meaningful relationships, but that’s been more of an esoteric thought, less “I wish I had gotten to date _______.”

     I was unemployed for most of this year with a brief temp job in the middle, but I’m currently working somewhere new and loving it. One of my coworkers caught my eye within the past two weeks, and I’ve been crushing hard on her. We brushed arms once or twice and it felt exhilarating, and I’m exceedingly attracted to her. This is the first time in my relationship with my partner I’ve actually liked another girl, and I really like this other girl. I don’t know her too well, although she’s friendly and funny and been fun to talk to. I think I’m mostly physically attracted to her, because that attraction’s strong. For the past week, I’ve felt like shit about this. I feel like an asshole, especially knowing I can’t say 100% I wouldn’t cheat on my girlfriend. I like to think I wouldn’t, but I can’t say I wouldn’t, and that makes me feel as worthless (I think, never cheated) as if I had done something.

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