Masochistic Experiences Part I: Dating and the Crisis of Masculinity

This post discusses heterosexual-cissexual dating. 


I arrived to the meeting place, a tea store, where we had agreed to see each other in person. It was not about his looks or his lack of education. It was about the entitlement. Initially, he conducted the date as if it was a job interview. He asked me a million questions, including why I was single. Being my first date since Saad’s passing, I decided that I had to rehearse the answer since I would probably be telling it quite often. So I did. He did not seem surprised. Instead, he decided to make witty comments about people who, unlike Saad, have been lucky enough not to die in car accidents.

Later on, he talked about himself. He told me how he had made it from Mexico to Canada. How successful he was. How he ran his own business. How he made tons of money and was a role model for the Latin American community. How he felt, at this point, that Canada was too small for him because he felt he was bigger than anything in either country, Mexico or Canada. And, of course, he did not let me forget that he thought he was quite the catch.


We decided to have dinner. Not Mexican because there are not good Mexican restaurants in my city. Not Asian because, as he told me, there are not decent Asian restaurants in the city either. So we went for Italian.

I wore the polka dot dress, and prepared to be interrogated like other guys had done before. But unlike the others, this guy just could not. He was terrified. He would not make eye contact and barely talked. Can I blame him? No. Dating is, as a friend recently told me, “a masochistic” practice.

It all ended within an hour. He was way too nervous. I was way too confused.

He eventually gathered the courage to ask me on a second date, and I agreed. Who knows! An awkward first date should not be the end of the world or prevent people from exploring a further connection. He took me to a very fancy restaurant, where even though I insisted on paying at least my share of the meal, he would not hear it. We talked a bit about everything. His dream was to buy a house in the suburbs, get married, have kids and live happily ever after. And although there is absolutely nothing wrong with that, all I could think as he talked was about my passion for writing, my interest in political and religious issues, and my definite dislike for the suburbs.

Out of all the guys I have met, he was the one who had the commitment part all sorted out. He was not scared of it. In fact, he was seeking it, something which is apparently quite unusual in the West these days.


We met at work. It was an instant attraction and an immediate connection. We bonded over religion and politics and discussed a lot about Indigenous issues, one of my interests these days. He was educated, had a job, and he was cute and interesting.

We shared a passion for ice skating and good food. The cherry on top was that he loved sweets as much as I love baking them. We initiated this flirtatious relationship where I would randomly bake goods and leave them in his office. He will then return the favour by leaving little tokens of his presence in my cubicle.

It was fun and exciting, and he was the only person whom I thought, “I can work with this.” But the “commitment” aspect of things was not there. It started by us never reaching the point of intimately talking about our own respective “baggage.” Then, it continued by us stopping seeing each other outside of work weekly. Eventually, he was a ghost who would occasionally reappear in my life. Some days he would show up wanting to talk. Sometimes he would bring me gifts, which at some point included a piece of jewellery, but that was it. There was never a talk about “us,” no expression of interest, no visions of the future. Lastly, it turned into a very awkward semi-professional relationship…


I do not share this as means of scarring people off. I do not tell you this as a way of venting (well, maybe a little). Yet, I must say that my experiences with dating has left me wondering about masculinities. In eight months, I have seen things that have left me puzzled and concerned about heterosexual gender relations.

Relationships (of all kinds) and our experiences with men are the themes of endless conversations with a wonderful and diverse group of women that I meet every week and that have become my rock as a single woman of colour in Canada. Believe me… dating requires a support group… Hence, we sit and drink tea as we share our experiences in the dating world. Whereas not all of us are heterosexual, those of us who are, have found that some men between the ages of 25 to 40 have a little problem: They are in crisis.

I have been on dates with guys who have lost my attention and evoked my rage after telling me that women often lie about domestic abuse. Also, I have been in touch with ex-Muslims, who criticized my way of practicing Islam, leaving me puzzled and annoyed. There was the Christian missionary on a quest to rescue the world from Islam. There was the guy who told me that it was too bad the British had not exterminated Aboriginal peoples in Canada.  There was the guy who loved that I was “Latina” because in his fantasy world, I would be “easy.” There was the guy who aggressively yelled at me during a heated conversation because he claimed that sexual violence is a conspiracy to make men look bad. And there were countless others that just did not know what they wanted.

In addition, many don’t know what they are looking for in a relationship. In fact, many will go on into dating sites only to tell women that “they aren’t ready for a relationship.” Some others think that they can do better, but that they may “settle for you” if you “appreciate” them enough and to their liking. In other instances, they will appear and disappear from your life as if they expected you to wait for them to be ready. But above all, most of them expect the women they are “seeing” to abide by traditional understandings of relationships, love and marriage. Yet, they want them to be “modern,” “educated,” professional working women (but not too high up the ladder), with touches of sexy…

There are many heterosexual women who want the traditional marriage thing with the picket fence. Nothing wrong with that. Assuming, though, takes away choices from many women and it is an expression of male privilege. Not every woman wants a heteronormative monogamous relationship, or a marriage, or a relationship in the traditional sense. Not every woman of colour or faith going into the dating world is looking to get “exotified.” Not everyone is looking to make a man “settle down.” And not every woman looking for a heterosexual relationship is looking to “settle.” Yet, in thinking that’s the way it is, we learn more about how societies have changed, but the roles and expectations haven’t caught up to that. Some men just cannot conceive the idea that some women may have diverse expectations, and do not know how to interact in a world where women want different things. Basically, some of them just don’t know what to do in a world where some women have the opportunity to break the mold of traditional heterosexual relationships.

What are men to do with women who do not get flattered when they are told “Latinas are sexy”? What are they to do if they aren’t expected to pay for dinner? How can they deal with women choosing how sexual contact will or will not happen? And how can they understand that many women these days are looking for things that the traditional model of heteronormative, patriarchal marriage does not offer?

Thus, dating in a heterosexual context, ends up being a “masochistic” experience where we face a clash of expectations not only between two people, but between traditional societal norms that may not reflect our realities. Yet, these days, if you want to find a partner, companion, husband, or something in between, you need to put yourself out there. The question is, can that process and our exposure to societal changes give us what we are looking for as women, especially as women of colour?

To be continued… Part II.

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