Sex. Celebrity. Politics. With Teeth
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Sex. Celebrity. Politics. With Teeth

I'm 29 and I've Never Had a Girlfriend

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Illustration by Jim Cooke/GMG.
Illustration by Jim Cooke/GMG.

Dear Jane,

I am a man of color and I have a bit of a problem approaching women. Perhaps a female perspective outside of my circle would be most beneficial.

I suppose I should tell you a little about myself. I’m 29, an engineering tech and I’ve never had a girlfriend, ever, in my life. I keep waiting for my “moment” like it’s a RomCom video or something, but I know I have to make the moment myself. The problem is that I have a bit of approach anxiety.

I know catcalling is wrong, I’ve actually been on the receiving end of it, and it didn’t feel good at all.

I also don’t have a problem being rejected; it’s hard for us guys to be vulnerable, and I feel embarrassed, but I never wanted to hurt anyone because of it.

Every time I think about approaching a woman I’m interested in, I see myself turning into my father, or rather, the chest-thumping neanderthal he tried to turn me into. I’ve read a lot of articles and listened to a lot of feminists talk about toxic masculinity, and let me tell you, it all applies to him.

He has called my mother and my brother (not me, ‘cause I’m not giving him my number) in the middle of the night to have a temper tantrum. But I’m the soft, emotional one.

He once pulled me out of his truck and threw me on the ground because I jokingly said I could take him in a fight when I was a teenager. (It doesn’t matter what I said, I was a child, you don’t do that to a child.)

He’s made fun of my weight, told me to lift weights, and offered me cigarettes when I would do yard work with him.

He wanted me to fill out a job application for him, I told him no, and said I didn’t want to have a relationship with him anymore, he then hung up, called back, and said that I had to have a relationship with him because he was “paying for me” i.e. back child support.

He has repeatedly questioned my sexuality because I don’t chase after every woman I see. He went out of his way to make me feel inferior because I wasn’t an athlete or work in manual labor.

My dad is pretty much a short black Donald Trump without the money.

This is the man I’m afraid I will become, the man whose influence I have to fight everyday. I’ve been in therapy for a while, I plan on going back, but I feel like approaching women is the last hill I have to climb. So, for a while, I resigned myself to being alone, but I really want to try dating.

I know that this a lot to process, so if you don’t have anything for me, I understand.


Veteran of the Psychic Wars (oh please, don’t let these shakes go on.)

I love you. You are the man of my dreams. Just keep being yourself and get out into the world in whatever way you can so that more women will get the chance to know such a wonderful person.

Many, many people have this same sort of anxiety about approaching women (though often not for such thoughtful reasons as yours). Have you tried internet dating? You seem like the exact right guy for Bumble, the dating app. It’s incredibly popular so forgive me for explaining something that you probably already know, but this is the dating app where women approach you, not the other way around. Perfect for hesitant dudes such as yourself. If you’re in an area where that app doesn’t really work, you could set up an OkCupid account and if I were you, I’d put all of the personality you shared here into your profile.

I’m sorry your dad’s influence is still so strong; it takes a lot to shake that, but you’re doing the work and well aware of it, which is more than most folks can say. You’re a fucking catch and don’t need to worry about approaching anyone. Be you and the right person will recognize a gem when they see it and work their ass of to make that gem theirs. I promise.


Dear Jane,

I have been dating an amazing man for the last two years. We are both in our early 30s and very much on the same page about what we want in the long term (marriage, kids, etc.). He is the best person that I have ever dated—kind, intelligent, affectionate, honest and he makes me feel like I can always be my authentic self. However, I am from Canada and I very much want to move back eventually to be near my family, especially to have kids. He is resistant to this idea for two main reasons: first, his career prospects/the fact that he spent a lot of money on an education that is seemingly applicable to the US only and second, his close relationship to his mother.

Having the support of my mother and close family & friends when I go through pregnancy, labor and the crazy first few months after having a baby is so important to me that I might even call it a dealbreaker. Add to that the maternity leave differences between US & Canada (Trudeau just extended mat leaves to 1.5 years in Canada vs the three month standard in the US), and I feel even more set on heading home for this critical time in our lives. And it doesn’t even need to be permanent or forever.

I don’t want to jump the gun since my boyfriend & I aren’t even engaged but this is definitely a path we are headed down, except there is this huge question mark standing in our way. We are approaching an age and stage in our relationship where this factors into our next steps. I know moving would be a huge sacrifice that he would be making for us, but I believe in my heart that this would be the best decision for our yet to be family, not just me as an individual (we would have an enormous support system—financially and emotionally). I would even invite his mother to live with us if that would help make things easier for him; she is truly wonderful. I guess my question is this: is it unreasonable for me to ask my boyfriend to move, at least for a few years during this time in our lives? And what does that say about him if he is unwilling to do so?



This part of love is uniquely thrilling—the imagining of a perfect future and family.


Your Canada setup sounds AMAZING and I am so jealous, personally, as a mom from the US who lives nowhere near family. I can see all the reasons you’d want to be there for that time, but you’re kind of jumping the gun and being a little unfair to your dude. First of all, like you said, you’re not even engaged and are talking about something that is still years down the line. You could be dead by then! Try to be more grounded in the here and now. Instead of focusing on this one hypothetical thing, work on strengthening your connection with your partner. Maybe in a couple of years, after you know each other even better and you’re more attached, he’ll be up for said move. If a year or five from now he’s still digging his heels into US soil and you are ready to get pregnant and give birth across the border, time for a new boyfriend. It will be heartbreaking but it won’t be too late and you’ll have had some very wonderful years with “the best person” you have ever dated.

Also, in that time you may change your mind. Your parents could turn evil or Trudeau could turn evil or YOU COULD TURN EVIL. Give it time and enjoy your relationship for what it is and where you are right now. Who knows, you might not even be fertile?


Dar Jane,

Long story short, I left BYU Idaho two years ago, moved away from my parents in Wisconsin, and started living in Utah to come out and start purging dogmatic beliefs from my life. Last night, a relationship of six months ended. Let’s call him Jared, and say he considers me his best friend, and says I’m not emotionally or romantically satisfying.

A former roommate used to call me a “cuddle whore” because he said I’d curled up with every gay guy in Utah county (safely, because I’m a practicing virgin). Even with how many people I’ve gone on dates with, I’ve literally, as in “not figuratively,” never met anyone like Jared—core theologies are the same, and just finding a gay who is, no offense, not an avid Democrat or struggling Mormon, seems impossible.

Time for shock therapy to start dating women so that I can select from half of the population instead of one percent of the one percent?


The .0001 percenter

Someone reading this knows the right person for you and can email me and I’ll put you in touch. But! If I’m doing my math right, you’re only 24. You’re doing everything fine (except the part about where you live, you should move!). You’ve had a serious relationship already and that will happen again, promise. Yes, you are a rare breed and that makes the pickings slimmer, but you aren’t even done becoming who you are going to be yet so don’t pigeonhole yourself into that tiny space. Who knows, maybe you’ll end up marrying Jared when he snaps out of it?


Have a question for Jane? Email her at Please change names and identifying info; this advice column unfortunately is not aimed at destroying lives.