Tag Archives: Dating

As of August 28, comments are closed. Letter Writer: Go read some books by women, try out some new social activities, GO TO A REAL THERAPIST, and be well.

Dear Captain Awkward,

So I’m a guy, 20 years old and totally devoid of any form of romantic relationship. Ever. I’ve never so much as held hands with a member of the opposite sex, never mind anything else. I’m getting incredibly lonely and yes before you say it, I did behave like a nice guy tm once and just once. I was an ass, I made an incredible fool of myself, I traumatized my friends and worst of all, I hurt that poor girls feelings. She wasn’t the nicest person and took advantage of me, but I hurt her feelings and I made sure when I came to my senses that I apologized, regardless of what she’d done, I messed up. Before all that happened, I was an incredible jerk, an arrogant piece of shit with an intellect to match and zero attachments to anyone. I hated the idea of feelings and I shut them out and didn’t do friends (ironically this is when I received most attention from the females). For most of my teenage years, I didn’t need people and I didn’t need love.

I’m literally petrified of making the same mistake again and of ever hurting another living soul again, I’ve been bad, I’ve made mistakes and I’ve taken advantage of people, now I’m trying, very hard not to be that person again and that includes treating women as people, with thoughts and feelings, hopes and fears and dreams. It’s difficult in the uni dorm I’m in, considering most people I meet socially are either drunk (I’m stone cold sober) or do the whole ‘one night stand’ routine which to me is appalling. The few people I’ve really sparked with are all in relationships.

I’m lonely and very different, I’m eccentric, have eccentric tastes and I’m a lot more mature then most people I meet in most social settings (I’ve been regularly mistaken for 40+ when I was 18) I’m also a romantic whose entire cultural upbringing utterly rejects the idea of genders freely mixing and all that cabal. Pretty much means my social skills are shit. I can out-argue almost anyone and I can debate exceptionally well but I’ve zero social skills that aren’t an argument, sports or one of my passions (which many people do not like) I’m regularly putting my foot in it in casual conversations and I have been told in the past that I am far far too intense. 

On the plus side, most of my closest friends are all female (I do not and have not had romantic feelings for any of them) and they’re great people but they all offer conflicting advice on what my problem is. I’m fast becoming isolated, I’ve zero self confidence and my self esteem has taken a nose dive, a combination of truly looking into the mirror for once and a mystery illness. I don’t think I look handsome, but a lot of people have said that I do. I get really confused and I pick up a lot of body language, but I have no understanding of social cues. It’s like I’m trying to read Swahili.

What on earth is wrong with me? Am I incapable of being loved?

Awkward & Lonely

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Thanks (?) to the nice Twitter friends who clued me into this horrible WikiHow on How To Stop A Wedding, or, as @KristinMuH put it, “a manual to help stalkers ruin their target’s special occasions.”

While I once joked that I would like to see this happen someday, it was, in fact, a joke. And the instructions to basically kidnap the person make my hair stand on end:

Take charge if things go your way. If he or she decides not to go through with the wedding, it is your duty to immediately escort the bride/groom away from the pressure of their family and friends. There is no doubt that friends and family will be angry or furious and will demand answers if the bride or groom doesn’t immediately flee the scene…Have a get-away car prepared so that the bride or groom doesn’t have to face the embarrassment of his or her friends and family.


So, if you find yourself searching for instructions on how to stop a wedding, ask yourself:

Has the affianced person been kidnapped? Is it a child? Then stop the wedding by alerting the appropriate authorities.

Is this someone you think should marry you instead? And they know how you feel? And yet they are still obstinately not marrying you, to the point where they have planned an entire wedding with someone else? Okay, here’s what you do:

  • Find out when & where the wedding will be.
  • Book yourself a vacation to “anywhere but there.”
  • Block this person in all social media spaces so you’re not seeing photos and updates.
  • Try for someplace with very limited internet access so you reduce temptation to watch it unfold on real time at the wedding hashtag or whatever.
  • If you can, get a trusted friend to go along with you so that you are not alone and there is someone who can comfort and distract you.
  • Remind yourself that soulmates aren’t real, and that other people get to choose who they want to be with.
  • Or, if it’s more comforting, say to yourself “They are making a mistake, but it’s their mistake to make.
  • Wait it the fuck out and move on with your life.

And if someone pulls this whole shebang on you at your wedding, here is a script:

“This is inappropriate and I’d like you to leave now.”

Hopefully your friends and family and security will form a nice barrier between you and this person and make sure they are escorted from the premises.

Now it’s time for the monthly(ish) feature where we find out what search terms bring people to this site! Except for adding punctuation, these are unchanged. Enjoy!

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The monthly(ish) roundup of the questions people type into search engines to find this blog.

1. “My partner thinks I have genital warts but I have herpes what do I do?”

Both of you should get a full STI screen, if you haven’t already, and talk about whatever you find there. (‘Cause maybe it’s both). Or, if you’ve just done this, say “We thought I had HPV, but the screen showed that actually it’s herpes. You should get screened, too.

2. “My girlfriend is rude to my parents.” 

“Hey, you were pretty rude to my parents tonight. I don’t appreciate you (specific rude thing she did). I think they deserve an apology, and I need you to calm that whole thing down.”

If you bring it up, does she acknowledge the behavior? Is she rude to other people who aren’t you? Is she rude to your folks even after you talk to her about it?

3. “I joined a dating website to hurt him.”

Spite Dating: seems totally reasonable and like it will bring you and your Spite Dates nothing but happiness!

Or, ahem, maybe this is a good sign that whatever relationship you’re in has run its course and it’s time for you to find the exit, take some good care of yourself, give yourself some room to mourn and heal. Join a dating site to remind yourself that you have options. And then, when you’re ready, use that dating site and find new people who will be into you the way you want them to be. But do it for yourself, not at your (soon to be) ex.

4.” ‘I love you as certain dark things are to be loved in secret, between the shadow and the soul’ what does the line means?”

Reading the whole poem, it seems to me the poet is describing a love for someone for reasons that would not be obvious to everyone, in a way that isn’t necessarily healthy or a good idea, but is true nonetheless. It reminds me a little of the song My Funny Valentine. Lit Majors of Captain Awkward, what say you?

5. “I just don’t feel ready enough yet to be in a new relationship because I’m tired and now I want to be alone.” 

Embrace the alone.

Make your living space exactly what YOU want it to be. Eat foods YOU like, watch movies YOU want, listen to YOUR favorite music. Throw yourself into work, into school, into creative endeavors, into meeting new people or trying new things for their own sake. Or curl up under a blanket and wait out this eternal February with a good book. Spend time with your friends and family and people who love you. Be really nice to yourself. Heal. Get some rest. Feast on your life.

And when people ask, in a well-meaning fashion, if you’re dating anyone new or if you plan to, smile and say “I’m sure I will someday, but I’m really enjoying being alone right now.

There’s this picture of Katie Holmes from a while back that people were criticizing for being “frumpy” or whatever. I kind of love her outfit and would wear it in a heartbeat, but mostly what I want to say is “LOOK AT HER SMILE. THAT IS A PERSON WHO IS FEELING LIKE HERSELF RIGHT NOW.”

That’s you. Alone. Walking through the world like you know a secret no one else does, and the secret is that life is huge and amazing and you are strong and wonderful and there are all kinds of love in this world and relationship-type love is only one of them.

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Dear Captain Awkward,

I’m a white ciswoman in my late twenties living in the Midwestern US. I’ve had a free online dating account for a while, having marginal success with short term dating but nothing that’s really led anywhere. My only *serious* relationship ended five years ago, after less than two years. I’ve come to terms with being choosy, and I don’t think that’s a bad thing, but more recently I’d started to wonder if I was being too picky or not patient enough or something. However, this latest guy has me all excited and fluttery! However, he’s got some baggage that has me confused as to how best to behave.

During our back-and-forth he was friendly and engaging, we got on quite well, and even realized we had a female friend in common (which was like an instant recommendation). We’ve only had a few dates so far, but we seem to be clicking really well and it feels like I’ve known him much longer. I was already be a bit nervous about too-much-too-fast (scaring him off?), when he told me (over a few conversations) that he’s in the process of a divorce that’s ending a marriage of mutually-destructive maybe-verbal-abuse and disillusionment over their shared religion, and the split was less than 6 months ago.
(I know that some cheaters use “getting divorced” as a cover, but given our mutual friend, his social media profile and his dating profile, as well as my gut, I believe him)

I am not sure what I should be doing given his situation. He’s voiced worry he might be using me, and while I don’t feel used, I worry he might mean using me emotionally as a rebound (is a “rebound” even a real thing?). Ideally, I would be there supporting him to help him work through what he needs to work through for us to have a great and fulfilling relationship that lasts for a while and leaves both of us happier, but how wishful is that thinking? I worry that being in too much of a caretaker role would get in the way of being seen as a romantic partner, but should I worry? And mightn’t moving too quickly romantically lead to relationship collapse if he’s not as ready as he thinks? Can you help me balance my desires and his potential needs?


Wishing it would just work!

P.S. I don’t think it matters to him, but he’s in really good shape compared to me, so I also have that frustrating but common worry that he’ll suddenly notice and not find me attractive anymore, which is definitely contributing to my fear about coming across as too much of a shoulder-to-cry-on or too maternal.

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Mr. Collins from Pride and Prejudice

“”Believe me, my dear Miss Elizabeth, that your modesty, so far from doing you any disservice, rather adds to your other perfections. You would have been less amiable in my eyes had there not been this little unwillingness…” STOP RIGHT THERE, MR. COLLINS

Hi Captain,

I’m hoping you can help me with this because you and your army of Awkwardeers are – like my crush – awkward.

He is a gorgeous gorgeous man that I work with. I’ve only been there a few months but I noticed him instantly. I did my usual thing of kind of showing off a bit around him, but he never looked at me or joined in. He hardly ever speaks at work, and he doesn’t look people in the face – he’s a really shy, geeky type and rarely comes out with us when we go for drinks.

One time he did come and talked about how he hadn’t had a girlfriend for so long, he couldn’t remember. So I thought I had a chance.

We have a shared interest and I sent him a message along the lines of “Hey, want to go for drinks and talk about Shared Interest sometime?”

His response was pretty cold – “we can talk about it at work”. I just said OK and left it.

Some of my friends think he didn’t get that I was asking him out, but I think that plays to my vanity. Is he just really, really uninterested? I know he wants to be with someone because he’s mentioned it – but should I take him at his word and leave it, or do I need to take the sledgehammer approach because he doesn’t realize I’m interested?

Thank you, Captain!

Love from,

Not That Awkward Actually

Dear Not That Awkward:

“Would you like to go out sometime?” ==>”We can talk about it at work” is a pretty blunt redirect, especially since I’m guessing that your coworker did not subsequently bring it up at work and you have not since gone out. Going forward, I would interpret all communications extremely conservatively. He knows you are interested in hanging out outside of work. He knows you have a shared interest. He has all the information he needs to follow up, or not, as he wishes. Possibly it was a face value statement – Let’s talk about this later, at work! – and possibly it was a message of disinterest. Redirecting personal conversations so that they are work conversations is what we advise people to do when they are not interested in personal interactions with coworkers. I realize this is maddening, but you’ve done what you can. The upside is that if he brings it up, you’ll know for sure that he wants to hang out. Until then, drop the subject. Read More

Dear Captain and co.

This is a not-quite problem that’s separated into two parts.

I’m not interested in sex or dating/relationships. I’m not comfortable at the moment categorising myself as asexual/aromantic, although maybe at some point in the future if I find it’s convenient. Essentially I’m happy with the ‘’it happens if it happens’’ mentality, but would also be happy if it never happened. I’ve been left cold by the few encounters I’ve had in the past, and would rather focus my social attention on platonic friendships.

Basically, I suppose I’d like some reassurance that this is ok. I feel like I’m so used to hearing about being single in terms of a problem that needs fixing, a personal failure or just a transitory period, without so much of the ‘’relationships aren’t for everyone, and that’s cool too.’’ (Possibly doesn’t help that I’m female and like cats, which is another stereotype that annoys the hell out of me.) Also, any advice on how I could convince people that it’s not a problem would be appreciated.

I think partly because of this, I have trouble comforting/offering advice to single friends who want relationships. I don’t want to sound dismissive and say something like ‘’but really, you don’t need to be with someone’’, but also don’t want to fall back on determinist cliches of the ‘’it’ll happen for you eventually if you want it to!’’ sort, and because I have no first-hand experience of seeking relationships, I can’t offer up anything in that score.


Cool cat lady.

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A magic 8 ball that says "Reply hazy, ask again later."

I’m awkward, I’m not oracular.

Dear Captain Awkward:

So I went on a second date with a guy and am unsure of next steps. Context: both dates were Sunday walks where we were bundled up like marshmallows. End of first date – he’s very specific with his plans for following up. End of second date – a hug and ‘we should do this again sometime.’ Given his approach to the first date, I interpret this as ‘friends,’ but then he went out of his way to come back to my car and give my dog a treat. What’s your interpretation?

-Shy One

Dear Shy One:

My interpretation is that, while none of the interactions you describe sound like a brushoff, you are asking an impossible question.

There is exactly one person in the universe who can tell you about this guy’s feelings, hopes, plans, and wishes re: You and what he intended certain words and actions to convey beyond their literal surface meaning. He gave your dog a treat, so I assume he wanted to give your dog a treat. I don’t know the meta-meaning of dog treats or whether they carry some deeper Jungian significance for him or whether he was doing some subtle conveying in your direction. Also, you were there! If you can’t tell what the vibe was like, how can we?

Good News: You’ve met the person who holds the key to this secret. They will be easy to contact!

Bad/Scary News: It’s this actual guy!

So, do YOU think the date went well?

Did you have fun?

Did you enjoy talking with him?

Do you WANT to see him again?

Do you have feelings about him?

Are some of those feelings located in your pants? Is there at least a twinge of curiosity about his manly, well-formed hands inside those giant mittens or the pleasing lips you glimpsed through one of the holes in the ski mask?

Are you unsure about how you feel and think you need to spend more time with him to make a good decision?

What would happen if you emailed him right now and said “I had a great time seeing you the other night. I think you are very handsome and fun to be with, and my dog also likes you. Can we plan another date soon?

Pretty much the worst thing that would happen if you sent that message is that he does not feel the same way and does not want to go on another date. That was always a possibility (as it was always possible that you would not like him), so that possibility is eminently survivable, right? Look at you, surviving the idea that some random dude isn’t all that into you. Well done, you!

A second possibility is that he’s WAY into you but after another date or seven you decide you’re not into him. Also survivable; consider it survived.

Third possibility is where the maybe-happy maybe-risky maybe-good stuff happens. I don’t think anything you have told me takes that off the table. So be awkward and see what happens. But stop examining every word and action as if they are sheep’s entrails. Sheeps’ entrails don’t tell the future. Nor do a bunch of totally innocuous and routine social interactions from someone you just met.

Okay, I’m making some fun of the question, but I want to say: There are a jillion sites and quizzes and articles that purport to decipher routine innocuous interactions and tell you what He/She Is Really Thinking, or, Signs He/She Likes/Doesn’t Like You That Way. Unfortunately, these publications employ total dipshits to explain enforce gender norms. Behind anyone claiming to translate Boy into Girl or vice-versa, picture the proverbial emperor dancing around in his tighty-whiteys.

Good news! You’re definitely not stupid for wanting help processing something you’re not sure about or hoping that we might have reassuring answers! Bad news: Reassuring answers on what this guy intends are backordered, arriving never. Do people communicate desire in confusing, indirect, and nonverbal ways? Yep, all the time. Should you try to decipher all of those behaviors and look for “signs”? Nope. You’ll make yourself nuts. If you can’t tell, and they haven’t told you, and you want to know, ask. You may or may not be an object of this guy’s desire; you get to be an agent of your own.