The post title was the subject of the email exactly as it came to my inbox. That will be important later.

Hey there Captain,

I recently moved to a job that not only frees up more time to focus on schooling, but pays better. On the last day at my previous job, a girl I’d occasionally worked with and spoken with in the breakroom, asked for my number.

If her interest wasn’t obvious enough, as I walked out the door for the final time, her question was whether I had a girlfriend. I told her no, and to my amusement, her reply was that she’d text me. Needless to say, I got a text bright and early the next morning and we’ve been texting a bit.

She’s nice and I get along well with her, but I’m unsure about making the choice to date her. There are a few things I see as obstacles, but can be worked through.

She’s the daughter of my previous manager. Introductions as a boyfriend would be awkward because my manager didn’t want me to leave. I worked hard, kept a positive outlook, and somehow managed to get along with even the prickly people there. I lit up many people in that glum environment.

While texting, she obviously wanted to get to know me better, so I took the lead, organized a meetup, and we had fun, went for coffee, and wandered around the mall.

It was a great chance to get a feel for her personality, lifestyle, relationships, and maturity. When I asked her what she enjoys doing, she said that she didn’t really have any hobbies, but that she enjoys hanging out.

During the meetup, she spoke mostly about how she doesn’t like work, her parents are always mad at her, her exes (about two or three by how she spoke about them), and her life in general. After the meetup, she told me she had fun and wants to meetup again next week (the next free day she has).

Clearly she enjoyed my company if she already wants to hang out again. I asked what she wanted to do, and she said “I don’t know, I’m good with anything”. This bothered me somewhat, but I’m a big boy, not everyone knows how to be assertive.

When I asked whether she’s doing post-secondary, her answer was the generic “I hated school, so maybe I’ll become a cosmetician”. She agrees with whatever I say and doesn’t have a lot to say about her day, goals, or hobbies. That bothered me more deeply. I’m easygoing, so I spent time reflecting on why this information bothered me.

I have my life together. I’ve got a great part-time job to cover costs, university and my budget balances at the end of the day. I pursue hobbies such as photography, programming, hiking, and cooking. I’m on great terms with my family. I know myself well and what I want in a companion. This girl is wonderful, but it seems she dates as a form of entertainment; escape from her life. I date for a strong equal to share my interesting life with, and I’m not seeing a lot of that in her.

I’m not interested in being a crutch and I can’t save her from a boring life. If there’s a way for her to grow up and not rely on me to fill up her open schedule, I’m open to sharing a life with her. Although she’s my age (19), I don’t think she’s at the point where I can tell her this without grievously wounding her undeveloped ego, especially given how she admires me.

My first relationship (a different girl), about a year ago, ended because both of us had been insecure. Since then, I worked at self-improvement, and I’ve honestly been impressed with my progress. I’m a much more confident and relaxed person than I was.

I know myself well enough to know conversation is important to me. I’d feel lonelier in a relationship than alone if the other person had nothing interesting to talk about, AKA, their own life. I’m looking for a healthy relationship where our worlds don’t revolve around each other, but where we know there’s respite in each other’s company.

How can I kindly tell her that she’s wonderful and brave, but not ready to be the female lead in my story?

Casting a Female Lead

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Dear Captain Awkward,

After a very painful marriage breakup and over 10 years of not dating (for many reasons including mental breakdown, SSRI sexual side effects and being too scared to go back into that shark pool – and yes, I’m currently in therapy) I’ve recently started online dating.

At the end of a recent (first meeting) coffee date, the man indicated that he would like to see me again, but then rang a few hours later to say that he had changed his mind. I am totally ok with him changing his mind, but the call made me feel quite uncomfortable because he seemed unable to just say what he needed to say then get off the phone. I assume he was trying to be polite, that perhaps he thought it was more chivalric than sending a text message or email or just dropping off the face of the earth, but I would actually have preferred one of the more impersonal methods in this setting, where I hardly know the man and am never going to see him again anyway.

My question is whether I should be upfront about my preferred mode of rejection while we’re still just emailing or texting, or whether it’s silly and preemptively negative to bring up how we’re going to end things before we’ve even met, and I should just learn live with the fact that all rejection will be at least a little bit painful.

Scared of the Shark Pool

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Hey Cap, ive got some girl troubles i hope you can help me out with. So a couple years ago i got the pleasure of meeting a girl, me and her would hang out almost daily and we became very close, we were extremely flirtatious and everbody thought we were together. But a few months into our friendship our communication went a little cold and we stopped talking for a little while. I then had a brief relationship with someone, and so did she. Its now a year later and we have been hanging out again and i brought up the courage to ask her out. If i would of done this when we were closest back then it would of been an instant yes i believe. But now she is really hesitant, scared of being hurt, and losing me as someone she can talk to. I want some cold truth here should i keep trying or move on?


I’m so sorry that you seem to have missed the window on this one.

You saying “Hey, I’ve always really liked you and I’m glad that we were able to get back in touch. Do you think we could give dating a shot now that we’re both single?” is brave & cool. There’s absolutely nothing wrong with saying it, and there’s nothing wrong with her hearing something like that from a good friend and needing some time to process and perhaps mentally reframe things a bit before committing one way or another. I think the smart thing for you to do now is to treat anything less than “Hell yes!” as “No, thank you” and give her some space. “I had to ask, I only want you to say yes if you feel 100% great about it, so why don’t you think about it and we’ll talk in a few days/weeks/whenever you like.” Giving her and the whole matter some space will be good self-care and good care for the person you like.

It’s also a good tactic for getting to the heart of the matter. If she does like you back, if she is just sort of processing doubts aloud because she wants to be convinced, I think it’s good for you to bow out while she comes to her own conclusions and refrain from trying to convince her. People don’t forget being asked out by their friends, phones and email work both ways, and if her answer to your question a week from now is “You know what, let’s go for it,” she knows how to find you. You being respectful of her reservations isn’t going to lose you any points if this thing is meant to be, and if it’s not meant to be bowing out gracefully is a way of assigning yourself some grace and coolness points even in the middle of something that feels sucky and awkward.

Dear Captain Awkward:

I’ve been reading your blog and I really like your answers. Hopefully you can help me with a problem I’m having. I have no perspective.

I recently remarried (about 5 years ago), and my (second) husband’s parents treat me, and most especially my kids, as though we aren’t family. They don’t even really treat us as guests. It’s more that we’re accompaniments to my husband. He has two brothers, one remarried (but both wives provided ‘actual’ grandchildren), and one married for like 25 years; they, and all of their kids, are obviously all ‘family.’

But my kids and I aren’t. My husband’s mom, when my husband brought this up with her (that I was sad visiting because we weren’t talked to, and because I hoped we’d be part of the family), consisted of: “I’m not going to lose any sleep over (my sadness / my children’s isolation at their house)” and “blood is thicker than water.”

For the first few years, my kids would come with us when we visited, and were basically ignored (they might be asked a question, but then their answers were ignored). Their cousins were talked with, asked about school, etc, conversations ensued. My kids, on the other hand, weren’t treated overtly meanly, they were just ignored. My husband said to me, when I’d say it made me upset: “they don’t care about your kids, they just met them” and “it will take time” (yeah, forever, since nobody talks to us).

So, eventually, I told my kids they didn’t have to go when we go up (they are now 15 and 18, and my mom lives with us, so they can stay here). But honestly, I don’t want to visit either, since I also get ignored; I don’t want to leave my kids behind to be with people who don’t want anything to do with us. (I think this is because my husband is very close to my kids, they see my kids as a threat to the place of his daughter, since she’s ‘really’ family.) Pennsylvania is very different from Virginia in the concept of hospitality and family welcomes, I’m finding.

My husband will say “why do you NEED to belong?” like it’s selfish to want to be a part of the conversation. He says I want it to be “all about me”, but that’s not true, I only want it to be as much about me as it is about everyone. (Normally, he’s wonderful and supportive, but when we get around his family, suddenly he sees the sense in everything they do, and I’m crazy, and I should just be there to support him, and not care if anyone talks to me. He once told me to get out a “puzzle or something interesting” and hope somebody asked me about it as I sat and worked on it alone. He says me bringing up my kids is “pushing them onto people who don’t care.”).

Every Thanksgiving we’ve pretty much always gone to his parents, because my kids are with their dad, and I want my husband to be happy. But it’s harder and harder, after being married almost 5 years, to just sit and be ignored, and then have people be mad at me for not just sitting there contentedly. They’re happy to talk with me as long as I ask questions about them, but they won’t talk about me or my kids with me at all. Not true – they will ask one question about my kids, and when I answer, they change the subject. Like their duty was done, time to move on. So I don’t want to go.

To make matters worse, my husband’s 20 year old daughter, who essentially stopped seeing him once she became 18 (though happily kept taking his money) is going, and I’ll get to watch everyone be so happy to see her, even though she treats her dad so terribly, but then watch nobody ask about my kids, who treat my husband like a dad. I keep going hoping each time will be different, but it never will. I don’t miss my ex, but I sure miss feeling like a part of the family I married into.

So my options are:
a) stay home alone and let my husband and his daughter go be with ‘their’ family (this is the one I’m leaning towards) … sucks because I’d like a nice Thanksgiving with my family too, to begin to create our own traditions;
b) go, and feel isolated (we’ve tried the talking about it, it doesn’t work, this isn’t a family that talks about issues, or I’d want to just talk about it; my first in-laws, I’d talk about problems with them, we’d resolve them) – this is a “put up with it or don’t, but nobody’s changing”; or,
c) ask him not to go (but not really an option; they’re in their 80s, and I’m not going to keep my husband from seeing his parents when they don’t have too much time left).

Can you please help? Just give me a point of view other than mine or theirs? Thank you!

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From the “this can’t really be solved” files and the “I had a few free hours let’s knock some blog posts OUT” files. Hi!

Dear Captain Awkward,

I am having an issue with my boyfriend because he is having trouble deciding who he wants to work on a relationship with, me or his daughters mother.

My boyfriend has a 7 year old daughter her mother is coming back into the picture. She claims she wants to clean up her life from drugs and be back in their life. He told me she was degrading, flakey, cheating, and manipulative towards him. She would make plans to see her daughter and rarely sticks to them because she had been high. She had left my boyfriend and got pregnant, that man went to jail. She went back to my boyfriend and she did this up and back a couple times. Now she doesn’t talk to her sons father and wants to work things out with my boyfriend. He feels loyalty to her because it’s his daughters mother. With us in the begining he moved fast, i met his daughter the first few days of after I met him. He talked futures together and making plans for us, wanting to take our relationship as far as it could go. We have only been together 3 months but we spent much time together, got along great, I grew very fond of his daughter and she likes me. Recent weeks he has become distant from me, less talking, etc. Especially now his daughters mother is becoming more involved recently. He tells me he thinks what he and I have is a good thing. And he really likes me but now he is confused about whether working things out with her and being a “family” for their daughter is the right thing to do. Or if he wants to stay with me and move forward. It’s like he did a complete 180.

I honestly have no clue how to react or respond, I need help on what I should do or think.

Thank you from Baby Momma Drama

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Dear Captain Awkward,

Last year I ended a friendship “Joe.” Joe is a “misery loves company” kind of guy. He is also immature, manipulative, and vengeful. He will poke at your insecurities when HE feels uncomfortable, just so he isn’t the only one feeling vulnerable at the moment.
Example: I once confided in him that I felt like I was developing a drinking problem. He stopped me to yell about how I was obviously lying for attention and that claiming I had a problem was an insult to actual alcoholics. He then attempted to ban that subject from future conversations. Joe would have preferred keep me close, drunk, and unhappy than to risk me not hanging out at bars as often.
We did not stay friends much longer after that.

Joe’s character took a while to show through… and I’m ashamed to admit that it took me even longer to recognize I was being hurt. I just kept telling myself that it was my job as a friend to be there for him. I knew he was hurting and lashing out, and felt like a bad friend if I didn’t help him.

I soon realized that I was SO MUCH HAPPIER when we weren’t talking and I ended our friendship. I’m happier (and healthier) without Joe in my life, and I stand by my decision. I kept saying that my life got infinitely better when I realized that I could remove people from it. Maybe I took that too seriously with other friendships?

More recently, I ended a friendship with “Jane.” Our friendship had morphed into her using me as a dumping ground for her problems and emotions. Trying to “fix” Joe to the detriment of my own well-being was something I didn’t want to do again, and maybe it spooked me out of the friendship with Jane.

I pulled the “friendship fade-away” and distanced myself from her without much explanation. This, I admit, is not the most mature way I could have handled things. I didn’t want to hurt Jane, but I guess I was just selfishly ignoring what she must have felt about the situation. I kept telling myself that since I was fine, she must be, too.

I am, however, still happier not being her friend.

She has since made me the villain in this. She accused me of lying to her and trying to slight her on social media (untrue). She is avoiding me on the street and at work, and asks mutual friends to disinvite me to events. Did I really treat Jane so badly to deserve the punishments she is doling out? Am I the villain in this?

How do I take care of myself without being a jerk to others?

Thank you,
Selfish Sally

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Dear Captain,

A few months ago, two of my mutual friends/acquaintances split apart. They were quite close and while I don’t know a lot of details, evidence indicates to me (and actually both friends confirmed) that the friendship had turned codependent and one friend decided to make a permanent split for a variety of reasons that are his and I have never attempted to pry.

They live in different cities and my interactions with them never coincide. Luckily. I see them both regularly as one is my coworker, and I have grown a lot closer to the other as we started working out and playing D&D together on a regular basis.

My question concerns the co-worker friend. It’s looking like she is viewing me as her new bestie and I am worried because her behavior is setting off a lot red flags of bad/codependent friendships I had in the past where I essentially ended up becoming someone’s therapist and taken advantage of. I have done A LOT of work in the past year identifying my own behavioral issues in these friendships and setting up firm boundaries so I don’t get cast in the role of therapist for someone again, but apparently I messed up along the way to where I am now.

I have a lot of sympathy for my co-worker friend, as I understand that losing a friend is difficult. I had also split up with my boyfriend around the same time, so I could commiserate with her and the hardship of losing someone who was a huge part of your life and moving on. However, I was not prepared for an average of 8 to 10 texts per day, seeing each other at work, facebook messages, and the what not. Communication ranges from bemoaning her loneliness, ramblings of being upset at other friend, and also random bits about her life that I think would be more appropriate for a Twitter account or a handwritten journal. Most of time I just don’t know what to do with it or how to respond. I end up getting overwhelmed by the amount of messages and feeling suffocated/exhausted.

This behavior is very new and only happened after the cut off from the other friend. I don’t want it to continue and I feel very uncomfortable around her now. I am not good with people who come off as clingy. I get frustrated, frazzled, and there are many many instances where friendships either ended or relationships never got past the 3rd date because the other party demanded more of my time and attention than I could give them. I am highly introverted, I need a lot of mental and physical space, and I really really really enjoy being alone (this includes not getting lots of texts). This is How I Do Me and while she and I have known each other for a few years, she has never really gotten to know me well enough to know this. Our friendship level has been mostly at work, rarely hanging out outside of work due to living in different city issues.

I guess my question is two-fold. 1) How do I nicely assert to her that we have very different communication/friendship styles and while I think she is lovely person she really really really needs to stop because our friendship really cannot sustain this and 2) Is there a better way to identify these situations so that I can stop them before they start? I know this one seems pretty small, but I have ended up in several very intense and dramatic friendships that all went up in flames. I don’t know how I keep getting here and it’s beyond frustrating and upsetting.

Any advice would definitely be appreciated,

I am not the bestie you are looking for.

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