Tag Archives: Dating

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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African Violet, photo by on Flickr, shared under a Creative Commons attribution-noncommercial license.

Photo by on Flickr, shared under a Creative Commons license.

Dear Captain Awkward:

A year ago I broke up with a girlfriend of three years. Before she was my girlfriend she had been my best friend for over 10 years, and was someone whom I deeply trusted with pretty much everything. When we broke up it was very messy and she said some very hurtful things to me, things that, due to all those years of knowing each other, she knew would hurt me pretty deeply. And it did. But that really is not my core issue.

I’ve been suffering from depression for a couple of years (approximately 2 years), and only recently have I started seeing a therapist and taking meds to help me with my issues. And it has worked wonderfully. But those sessions have made me realize a lot of really troubling things about my past relationship. 

The doctor brought to my attention that her behavior had been pretty controlling and abusive towards me, even before we started going out. A small list of her behavior: she would get upset when I went out to hang out with other friends that were not her; also, if I had planned an outing with her and a few others, she would get upset that there were other friends there appart from her. If I liked things that she didn’t like, she got upset, same if I didn’t like things that she did. It got to the point that I would just agree with her so she would’t get passive-agressive with me. She also would get angry with me for the strangest things, like, messing up the structure of a sentence or misremembering the name of her college. She would start berating me for forgetting something so easy and so on. And on one occassion, when one of my friends was staying over at my room (I currently live in a college residence) because she was sick and her roomate wasn’t there, while i was skypeing with her, she got very upset and demanded that I tell her to leave, when I didn’t she got angry and hung up. I got so distressed over that that my friend took to leaving to her room whenever she called me via skype. And whenever I called her out on her behavior, for some reason, I would always end up apologizing to her for saying anything. And she could be so condessending towards me that she made me feel bad for things I didn’t feel bad for before (I’m really short, I don’t have a complex about it. But she once told me that she avoided heels when going with me so I would’t feel bad. I was hurt and for years I didn’t know why).

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Dear Captain Awkward,

My boyfriend and I have been going out for about a year and he is the best and I hope we stay together for a very long time. Lately (being about half a year) I’ve been dealing with feelings of jealousy. And not toward other women, he has never given me a reason to doubt his faithfulness. But I do get jealous of his time. We spend a lot of time together, and often when we’re not together we’ll chat over Skype. He feels very strongly that he requires time for himself, whether that means working on his own project while we’re hanging out or playing a video game while we’re skyping, making a back and forth conversation difficult. And I understand and am sympathetic to his need for personal space. But when it comes right down to it I end up feeling ignored and rejected. I want his attention to be on me when he’s with (or “with” in the case of Skype) me. I always promised myself I wouldn’t be one of these clingy, jealous girlfriends, and I try to fight the feelings when they arise but I can’t stop myself. 

And so, on an almost daily basis, I’ll start feeling a little abandoned. I will then say something or do something to try to get his attention. When he catches on he insists that I back off a bit. This leads to me feeling more abandoned than I did before. And then, in the most childlike fashion, I will throw a fit, which usually ends in tears until he comes to comfort me. And lately, he’s been getting so fed up with my antics that he refuses to comfort me, leading to greater fits, the most recent one almost ending in a panic attack.

I know that he is frustrated by my behaviour, and I am frustrated by my behaviour, especially as it drives a deeper and deeper wedge between us. And I always end up blaming myself which only adds to my already enormous anxiety. And I know that I am the one over-reacting in this situation, but I do wish the he would maybe be more sympathetic to how I feel and more willing to share his attention. I think his fear is that if he gives in an inch then I will take a mile (which, in all honesty, is possible). 

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Dear Captain,

I am in my mid-twenties and my fiancé died in early 2011. I coped better than I thought I would (he was sick for some time before he died so there was time to wonder) and have continued on with my life in many ways, but I do still miss him and think about him everyday.   I don’t think that’s a bad thing at all, I loved him when he was alive and I continue to love him now he’s not. However, friends of mine have recently, gently, been bringing up the subject of me dating again and I find I need some advice on this.

My fiancé was the first man I dated that I really felt I truly loved and could spend the rest of my life with, which is a rare feeling I think. However, I do think it is probably possible to feel that with someone else, although it might take a while to find him. My main concern is that if I did start dating again, I think I’d always be comparing the guy to my fiancé and, because my fiancé was a) a wonderful man and we just sort of fit together incredibly well and b) I tend to view him through rose colored glasses because of his death; the poor new guy would have no chance of measuring up!

I don’t think I need to start dating right now but I do get lonely sometimes and I am still only in my mid-twenties and hopefully going to be kicking around on this planet for a good chunk of time to come. Plus my fiancé and I had planned to have children and that is still something I would like one day. So, not necessarily right now but at some point I would like to find another guy to be with.

Although I have talked to friends about this topic I don’t actually have any friends my age that have been in a similar situation and older friends/family whose partners have died are at a much later stage in life and have chosen to remain single. I guess my main questions are; how do I deal with the issue of comparing guys to my fiancé? Should I be starting to date again now on the basis that I will always feel like I’m not really ready or will I eventually feel like the time is right? And if/when I do date someone new when should I tell them about my fiancé and how much detail should I go into? I am not generally someone who is very comfortable with sharing feelings with people I don’t know well, but I have no difficulty in talking about my fiancé, his illness, or his death in practical (non feelings!) terms. I don’t want to overwhelm someone with too much info in the early stages of a relationship but at the same time I don’t want them to feel I’m lying/deliberately keeping my fiancé a secret. That last question sort of applies to making new friends too, actually.


A Young (Not Quite) Widow

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Hi Captain,

I have a kind of strange problem. People say that I’m not good at expressing my opinions, but I think that is because I just have so few of them. I have some rather simple opinions such as “angelfish are pretty” and “all humans should be treated as equals”. Other than agreeing with certain political ideas and thinking things are pretty/taste good I don’t really have answers to lots of personal questions. The main issue comes up in social situations in which my opinion is part of the decision-making process. This often happens when choosing a restaurant or other social activity. It also happens when my boyfriend asks me what I want to do or asks “getting to know you better” questions. I always feel a bit bad when people ask me for my opinion on things and I say “I don’t know”, because it’s my understanding that “I don’t know” is the answer people give when they actually want to say “leave me alone”.

I have a couple questions about this situation:

1. What should I do about not having opinions? I’ve entertained the idea of making a notebook where I just list random things and then force myself to form opinions about them so that if anyone asks about things in that notebook I’ll have something to say. It seems a bit weird though because I seriously don’t care if we go to In-n-Out or Jack in the Box. It just seems like a weird thing to have an opinion about to me, but I guess most people expect to get an answer when they ask about it. So should I just formulate a bunch of opinions intentionally? It seems like most people just naturally care about stuff and automatically form opinions.

2. When people ask me for my opinion, what can I say instead of “I don’t know” or “whatever you want”? I really love conversations. I’ve typically gone with asking questions to the person I’m talking with, but there are some times where it doesn’t really make sense to do that. (like the fast-food question above.) I’ve thought that maybe I should just explain to people I interact with regularly that I seriously don’t know what I think about a lot of things, but it seems like that would come across as “I’m a shell of a person who has a very small personality”. The reason for that is because it seems to me like “personality” is formed out of many opinions, and the sum of all those opinions is what makes a person unique and interesting.

3. When people get tired of making decisions for me, they often tell me that they want to take my opinion into consideration because they feel bad for “never doing what you want to do” or “making you do what I want”. How do I explain to these people that they are not scaring or manipulating me just because they get their way all the time? I’d like a good thing to say that means “We don’t do what I want to do because I don’t care what we do” or “I always do what you want to do because I don’t care what I do (unless it’s dangerous)”. I think that people really think that friendships need compromise, but I don’t bring anything to the table for them to compromise with.

I just thought of another thing that might just confuse people. Would it help people understand better if I said stuff in the form of “My opinion is that you should decide where we go for lunch”? That way they understand that I’m not just letting them walk all over me or something.

Thank you!

-You can call me Kathy or Katie or Katherine or Kat. It doesn’t matter.

Dear Kathy or Katie or Katherine or Kat:

Would it be okay if I spelled your name with a C? Probably, right?

In answer to your questions:

1. I think having a notebook and writing about things you’re interested in is a great idea for anyone to do. Maybe it won’t generate a list of Conversational Opinions for you. Maybe it will just be you figuring out how you do feel about things. Try it and see – three pages or 750words/day is pretty easy to manage.

2. “I don’t know. I haven’t really thought about it,”  is a perfectly cromulent answer when you don’t know and haven’t thought about it. If people push you and push you for an answer, it’s okay to be irritated with them. You don’t have to have an opinion just to satisfy people who like to argue about things. Hold your ground.

3. Your #3 is where it gets difficult, especially when you’re talking about making plans. Your friends and family may in fact be worried that they are manipulating or steamrolling you or leaving out your opinions, but I think the key words in that paragraph were “When people get tired of making decisions for me…” and I think it would help to frame it that way.

I had a partner whose answer to “What should we have for dinner?” was almost always “Whatever you want!

Over time, that answer transformed into what what it really was, “I don’t care.

On the surface, how accommodating and easygoing he was!

Over time, it was totally fucking irritating. Because “I don’t care” meant that I had to do all the work of coming up with the plan. There’s actually a lot of mental work that goes into figuring out budgets and groceries and recipes and going to the store and then making the stuff and cleaning up afterwards. There is mental work in picking the restaurant, in making the plans. Not ever having or expressing an opinion means that you are always the passenger and the other people always have to be the driver. They want you to be happy, so they do the mental work of trying to figure out what will please you. Sometimes (as you’ve found out) it’s awesome to be the passenger.

I have a Friend who lives in (major city) who has some Family wanting to visit later this fall. Friend asked Family, “What do you want to do while you’re here?” Family said “We’re up for anything!

Super easy-going and pleasant, right?

No. Infuriating, actually. Because it seems Family is expecting Friend to act as a tour guide and do all the work of planning the visit.

You may not genuinely care where you go and what you do! But when you abdicate all decision making in your relationships, you are making your friends do all the work. It’s lazy! It’s uncaring. Your words are literally “I don’t care.” That’s not actually an awesome thing to hear over and over again inside a relationship. Because eventually you might start hearing “I don’t care, either, so I might as well go home and hang out by myself.

You know this is causing tension, which is why you wrote to me, and I do have a couple of suggestions:

A. “My decision is that you should decide where we eat” is passive-aggressive as hell. Do not say.

B. When offered two choices, just pick one (whether you have an opinion or not). “Do you want dim sum or Thai?” Since either one sounds good to you and you would be happy eating both, do the other person a solid. Mentally flip a coin. You’ll both eat. You’ll be happy. You’ll stop having the conversation you don’t like where people push you to have an opinion. The decision doesn’t have to come from the center of your soul.

C. Make a list of places you know you like to eat and stuff you like to do. On your phone. Or in your groovy notebook (which seems like a better idea all the time, so good job!). Read the local weekly paper and find out when movies are playing or neat stuff is going on. When someone asks “Where do you want to eat?” or “What do you want to do this weekend?“, name one at random. Sometimes people are tired and they have decision fatigue and the best thing you could do for them is to just steer them in some direction. Maybe you’ll say “Pizza” and they’ll say “No, I had pizza for lunch. Could we have sandwiches instead?” and lo, a decision will be made.

This may start as going through the motions. You really don’t care! Sure. Okay. So do a little work to find something that you think will please the other person, and be the one to take the risk and say “I think we should ________.”

D. Help your friends/family/partner communicate better with you. I have several sets of married friends where one partner is clearly the Alsatian, making the plans and herding everyone to the optimal good time, and the other partner is more happy to go along. Anecdotally, a few things seem to make this work:

  1. If A asks B, “What do you want for dinner?” and B says “I don’t know, whatever,” A gets to pick without further consultation. A should take B at their word that they have no preference, and B is not allowed to complain.  No back-and-forth!  To get this to work, tell the person you’re with directly: “If you ask me, and I say ‘anything is fine,’ take me at my word and pick something. I promise I’ll be happy, but we’ll both get annoyed if it becomes a long exchange.
  2. In some cases they spell out whose turn it is to (make plans/cook) on a calendar. This might work for you to give you some structure with your boyfriend.
  3. B partners recognize that what A partner does is valuable, and shows appreciation and also steps up from time to time. A gets to say to B periodically, “Hey, can you make the plans today?

Reading over this answer I am obviously biased towards opinion-havers. I absolutely don’t think you should be forced to have an opinion about current events or books or ideas and have to express it on demand the way I make my students do in a film class. That’s annoying and you are more than allowed to shut it down. But when it comes to planning basic things like where you’ll eat and how you’ll spend your time, I do think that by never expressing a preference you are slacking in your relationships. If you could get it to something like 70% They Choose/30% You Choose that would be an improvement. Over the long-term it’s not really fun to be around someone whose baseline is “Meh.”

Hello Awkward –

I’m a single father. I married my high school sweetheart and as a consequence, dated very little. So now divorced, I am thrust into this dating life and am finding my way. The dating part comes easy, being a gentleman and forming relationships has gone well. I get that part.

My question is when is it okay to introduce someone new to my son?

I have been very cautious about keeping him out of any relationships thus far. But, now I have met someone who I think has some serious potential to be around for a while. I don’t want to put either in a strange situation. My SO knows I have a son, and often asks about him and how things are. (Side note: she is a school counselor so I could ask her also, but that seems like it would be a strange conversation). We have been seeing each other for about a month, but have been much more involved than any previous relationships I’ve had.

You and your commenting followers always seem to have sound advice, so I ask….when do you think it’s right?


Learning As I Go

Dear Learning As You Go:

I know that it’s not about “amount of time” and more about “you think this person will stick around for a while and be a positive force in your kid’s life if they do.” It depends on the kid, and the person you’re dating. I know you’re trying not to make it weird for your partner in her professional capacity (and she wouldn’t know better than you, his parent), but I don’t think it’s a terrible idea to say “I’m thinking of introducing you to my son, what do you think about that?” and get her opinion as your girlfriend about whether she thinks it’s the right time.

I think the fact that you are being thoughtful about this is good, and am pretty confident that you’ll do what’s right. So I’ll turn it over to the readers who are parents or who have been in this situation. What should the Letter Writer watch out for? When is a good time to bring these two people together?


Ron Weasley holding a wand.

“Girlfriendio! I said, ‘GIRLFRIENDIO!’ Bollocks, why isn’t this working?”

Greetings captain! 

No matter what I do or say, I can’t get a girlfriend. I’m 18 years old, and I have never hugged, kissed, or been liked by a girl. I have never been on a date, or had any real chance of getting a girlfriend. I’m mildly autistic, I have ADHD, and am EXTREMELY socially awkward. I just want to be able to make a girl like me, and I don’t care how. Here are some side questions: 1.) Is there any way that I can pay a girl to like me? (I have a bit of $) 2.) Are there any drugs that will cure my social problems? 3.) Are there any “tricks” that I don’t know about? 4.) Do I have any hope at all?

Here is my dating profile: [[REDACTED]]

I just want to find a “miracle cure”. I’m tired of trying so hard, only to fail constantly. I deal with my emotional pain by taking Adderall (Amphetamine Salts) (I have an RX, but I buy more from friends). Adderall seems to be the only thing that will bring me a feeling close to “being loved”. I will continue to abuse amphetamines, opiates, and xanax until I get a girlfriend. I don’t care if I’m addicted, because it’s the only thing that brings me happiness. 


Dear Desperate Dude:

Holy shit, bro. Slow your roll. And/or your troll.

Ahoy, Captain! Maybe this is a pleasant problem to have, but it’s a puzzling one.

I’ve been spending a lot of time lately with a woman I find very attractive, trying to figure out whether I want to ask her out or not. We have a lot of interests in common, and do plenty of things together, but have different interests too. (I like this for a couple of reasons – the fact that she’s not into knitting means that my knitting group will always give me space from her, for example, and on the other hand she’s introduced me to a fun new sport I never would have tried otherwise.) I find her fascinating and really easy to spend time with – she’s just a very friendly person. I really, really want to make out with her, and from the way she’s acted towards me, I think she’d be pretty open to the idea of taking this from friendship to dating.

I’ve been holding back from that step, though, mainly because I feel I need to know people a bit better than I know her before I go there. (I’ve never been attracted to someone this quickly before – it’s both exciting and a bit weird.) It was actually a comment on a recent CA post that made me wonder if I should reconsider it altogether. I can’t find the comment, but it said something along the lines of “People who won’t respect your boundaries will tell you through their actions – they’ll touch you without asking, they won’t notice when they’re interrupting or dominating the conversation, and they’ll tell you inappropriately personal things.” That pretty much describes my friendship with her so far.

There’s a lot of physical affection in our friendship, which I love, but it did start with her touching me without permission – I just didn’t care, because I liked it. When something’s bothering her, she does tend to steamroll over other people in conversation until she’s exhausted her need to vent. And we hadn’t gotten to know each other for very long before she hinted to me that she’d been abused and lost most of her friends over it, though she only recently told me all the details. But although I was sympathetic, even at the time I thought it was a big leap to even drop me hints about this stuff when we hadn’t known each other long.

Captain, I don’t know what to do here. I really feel for her over what she’s been through recently, having survived the same kind of abuse and subsequent loss of support network myself. I want to do what I can to support her through that, and it’s clear she still has a lot of feelings to work through. But I do worry about some of these things, especially the way it’s almost impossible to get in a word in with her when she’s upset about something. It seems like the sort of thing that should be a red flag, or at least a warning to be careful while I continue to support her. And yet, I really like her! She’s very attractive to me in all sorts of ways, I love being around her, and she gives me warm fuzzy feelings in a variety of body parts. I just worry that my happy feelings are drowning out warnings I should be listening to. Or maybe that I’m just a bit desperate – I’m a lesbian and it’s really hard to find queer girls I can talk to in my area.

How do I tell whether to ask her out or not when my logic-brain says to be cautious but the rest of me just wants her?

I’m going to answer a question with a question and then let the commenters have at it.

Is there some reason that you cannot casually date this woman?

As in, be friendly, enjoy what there is to be enjoyed (ahem), but don’t try to lock her down as the Love of Your Life?

You’re smart to pick up on some of the red-flaggy behavior that’s not what you want in a partner, and you’re smart to not let the pants-feelings cloud your judgment, and you’re generally smart to be cautious, but I think the script you’re looking for is:

Would it be okay if we made out sometime?

And when she’s dominating the conversation, the script is:

“Hey, I’m sorry you’re sad. Is it my turn to talk yet or is this more of a monologue situation?”

I know you’re trying to be a good citizen of Feelingstown, but you can’t control everything that will happen and everything that everyone will feel. Definitely not all pantsfeelings need to be acted on, but you’ll never be this young again and obviously you both want to. Sometimes that’s a good enough reason.

Okay. Enough of being the devil on your shoulder. If your gut really says to not get involved with this woman for some reason – she just reads like Trouble to you – then listen to it, and put a stop to the flirty-touching stuff. But there’s nothing wrong with wanting someone, and there’s nothing wrong with wanting someone who you don’t necessarily end up with in any kind of serious or permanent way.

Shameless Plug Alert: Our friends at King Is A Fink have a new webseries out. Watch the trailer here. The After Ellen reviewer called it “one of the most heartbreakingly authentic stories about LGBTQ youth I’ve ever seen. It is The Misfits meets Skins meets modern-day Dickens, if Dickens had grown up gay and gotten his hands on a video camera.” It’s up our collective alley, I think.

A couple of weeks ago I started dating this guy. One evening we were with another couple and he was doing whiskey shots with one of our friends. He seemed sober and I didn’t think anything of it, but he texted me later to apologize, which I thought was classy. That was our fourth time getting together and the first time we were intimate.

We had a date planned for tonight. Last night I was home alone and under the influence of an intoxicant. I told him I wasn’t really up for chatting but I was looking forward to tonight. Half an hour later he called again and dumped me.

I think it was hypocritical of him, and not doing me the courtesy of having a sober and preferably in-person conversation was immature and tacky. He thinks we weren’t serious enough for it to matter. Am I being unreasonable?

Last week, we all agreed that the text-message breakup of a serious long-term (they lived together!) relationship was in poor form. Because it was.

In the early stages of dating, only a couple of weeks in, I can get behind the e-breakup or the phone-breakup.

Rejection sucks. We tell ourselves the lie that it would suck less if the person had just handled it differently. So, I’m sorry that happened to you. It sucks. You absolutely did deserve a real conversation while both parties were sober and I understand why you’re pissed.

But if he’d sat you down in a velvet booth and explained it to you gently while looking deeply into your eyes, you’d still be just as dumped as you are right now. Once the sting of rejection relaxes a bit and you’ve had a chance to move on, maybe take what happened as a gift. He broke up with you in a crappy way that shows that he would have been a crappy partner for you in the long run. Get good and pissed off! It lessens the temptation to pine.

Wanting him to apologize for how he did things is understandable, but engaging with him further to get the apology isn’t going to bring back the good times. It’s just going to keep you engaged with a person who treated you badly.

I’m sorry. It sucks and it wasn’t your fault and you deserved better.

Jedi-buying you a Jedi drink,