Tag Archives: Asking people out

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.


Ahoy, cap’n!

So, I’m a fairly attractive and well-socialized guy with a self-esteem problem that makes it difficult for me to assert even that I’m fairly attractive and well-socialized. For the most part I keep that under control, but romantic situations are challenging.

Being fairly attractive and well-socialized, I don’t have much trouble meeting women. Many of my friends are women. The problem is getting from being friendly to being physical.

I’m not the Mayor, and this isn’t another friend zone complaint. “Friends” is easy and comfortable, and “more” is — or feels — complicated and scary. I don’t know how to get there, I don’t know how other people get there, and much of the time it seems better to stay put.

What am I supposed to say or do? How do I know when to say or do it? How do I avoid panicking or feeling skeevy?


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Hi Captain Awkward-

Long-time reader, first-time writer, etc. I have a question that does not appear to be covered by your existing advice about asking guys out. I am currently a student (grad, not college, if that makes any difference) and I have a crush on my TA. I’d really like to ask him out, but I haven’t had any interactions with him outside of class, and am running out of reasons to go to his office hours. I’m also unlikely to see him again after I finish the class, because he’s graduating soon. I don’t want to make things uncomfortable while he’s still responsible for me, but I’m not sure if I’ll even see him again after classes end, and I know I want to know, one way or the other. What do I do?

Oh, and I’m also not certain he is gay. Though that’s much less of a concern than the timing, for me, I guess.


You guys, I’m buried in work right now, so keeping it to the short & sweet ones for a bit.

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Friday is my birthday.  In lieu of presents, there is something I would like (many of) you to do for me.  Given that A Shy Guy Caught My Eye is the most-viewed post on this blog so far, I’m guessing that more than one of you can relate to this comic:

If you read and thought “Oh man, that’s me.  I like ___ so much, but I don’t want to ruin our friendship,” do something for Captain Awkward.

Just ask ____ out already. On a date.  A real, live date.  A DATE-date, where you make it clear that a date is happening between two people who are on a date.  With each other.

Listen:  Chances are very high that _____ already knows how you feel or at least has picked up on your Firthing.

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Dear Captain Awkward:

There’s this boy.  He’s cute.  He’s also super-reserved.  Do you have advice on making a connection with incredibly reserved, hard-to-read people? I am a lady, for clarification purposes.

If you met him in a karaoke bar, your way is clear:  Sing this song and then buy him a drink.

I’m guessing that you did not meet in a karaoke bar.  And that possibly if you sang this song he would not know that you were singing about him, or if he did he would be terribly self-conscious and his ears would go all pink in that way you like, but you would be no closer to actually, um, dating.

There is no one right way to approach someone you are interested in, and a lot of wrong ways.  Your question makes me overjoyed for two reasons.  First, because most dating advice in the world assumes that it is the man’s job to approach women and the woman’s job to make herself approachable.  Men=Agents.  Women= Objects.  Gross.  Second because it is possibly my destiny to create a dating guide for people who are geeky and unconfident but really sexy and cool once you get to know them.  Since we still have ten good years before the robot ladies replace us, let me get on that.

I think I might be the person for this job.  Because:

  1. I am geeky and not particularly conventionally pretty.
  2. I am terrible at both flirting and noticing when someone is flirting with me.
  3. Yet I have somehow dated a lot, both successfully and unsuccessfully.  And by a lot, I mean A LOT.
  4. Since I have no ability to flirt or have sexy banter of any kind, my approach basically boils down to “We’re both humans, let’s talk about stuff that interests us, and if that’s fun, let’s keep doing that until making out is either on like Donkey Kong or clearly not in the cards, in which case, friends?”

Believe me, I was not always this cool.  My approach, circa 1988-1998, went more like this:

  1. I like you.
  2. I am filled with SHAME, CONFUSION, and LUST.
  3. So, when you are nearby, I will ignore you!  But in a very obvious way!  Or I will pick an argument with you about something stupid!  And you will somehow know that means that I like you!
  4. I will become overly invested and have an entire relationship with the version of you I constructed in my head.  We will have long conversations, that Head-You and I, until one day it becomes too much and I must relieve the pressure–
  5. By cornering you and blurting out my feelings, or worse, writing you a letter that lays out my feelings and a thorough and airtight case for why we should be together.
  6. And then giving you that letter.  Slipped into your locker at school, or in one case (EEK!) having your roommate lay it on your pillow.

And before you go “Oh, god, are you a crazy person?  Who acts like that?” (Which, dude, I know, and it’s possible that some of those letters are still out there and someday I’ll be, I don’t know, accepting an Academy Award for Best Adapted Screenplay, and some dude I had a crush on in 9th grade will be like “Hey internet, here’s the obsessive stalker mash note she snuck into my Latin book one time!”), I’ll tell you who acts like that. Read More