The Dating Coach

How to Lose a Guy in 10 Days: My Way 

A professional matchmaker makes every mistake in the book, and owns up to it

By Allie Roodman  November 7, 2023

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In the movie How to Lose a Guy in 10 Days, Kate Hudson’s assignment is to get Matthew McConaughey hooked, then get him to break up with her in 10 days by doing every no-no in the book that would drive any man — any sane person — crazy. This social experiment would be a cruel prank to play on anyone in real life. About a month ago, I unwittingly started my own version of this challenge. Luckily for me, I learned that I don’t even require guidance from co-workers on how to lose a guy. It just comes naturally. 

I was recently set up with a great man. Any woman would want to date him. Any guy would want to be him. Ivy-league educated and a former pro athlete, he now works in the sports world. He was cool, funny, sweet, and humble as pie. And the Tom Cruise resemblance didn’t hurt, either. 

We’ll call him John. John is in his late 30s. I am 31. 

Over the course of three weeks, I successfully blew up a budding relationship and pushed John away by coming across as a nightmare dressed like a daydream. These were on the spot, because-that’s-what-I-was-feeling, altercations. Credit the athlete mentality, because John actually held up well under torture.

I sent him a survey of questions about his intentions after the first date. After the third date, I sent an aggressive text calling him a coward. I openly talked about other guys I was dating. I told him he was being disrespectful for ignoring me. In my send-off text, I actually lectured him on how to pursue women. 

I’m a seasoned dater and have years of relationship experience. I even offer dating advice at the matchmaking company I work for. So why was I making mistakes and popping off like I would in my early 20s? What was my problem? And why was I so irritated with a guy who had been nothing but a perfect gentleman, an actual sweetheart, whom I liked? 


I Knew You Were Trouble
After a fun first date, John told me he was shy and asked for patience. I appreciated the heads up. “That’s OK,” I reassured him. My Uber arrived, and he texted me later that evening. Lying in bed, I felt happy. Finally, it felt like I had met someone worth exploring.

On our second date, John made me dinner at his place. We dug deeper into our relationship history and talked about things we valued and wanted out of life. “I don’t chase girls,” he said. He wasn’t being cocky. He was earnestly advising. I understood the message. No problem, I thought to myself. I can work around that. 

Later in the evening, in a more intimate moment, I was able to catch a glimpse of how far away he really was. “Wow, you’re really locked up,” I joked. He nodded. “It’s OK, I’ll crack you,” I teased. He replied: “No, you won’t.” I thought we were just being playful. In retrospect, I now realize things were already primed not to work out.

Our third date went well, but back at his place, I started to feel insecure. He was difficult to read, closed off. Nervous, I asked, “Do you have feelings for me?” I was pretty sure he did, but I’m someone who needs to hear things. “Yeah, I do,” he replied. It felt sincere but distant at the same time. His mixed social signaling confused me. 

I left his place with a sinking feeling in my gut. 

In the days that followed, I came to a fatalistic conclusion: I didn’t think this was going to work for me. 

I felt like any relationship that was going to develop would have to be completely around him: the pace, the amount of communication. It felt like a tilted stage. I felt pressured to open up about myself, though he expected me to understand that it would take him longer. The disparity unsettled me. 

In hindsight, when he was telling me how to work with him, I could have done the same thing. Maybe we could have come to some sort of compromise. This is what I would have said: “Hi, I’m Allie, and I have OCD. In the beginning of relationships, when things are very gray, I get anxious. I need a lot of direct, open communication.” 

I guess this is what my gut was telling me: This is not who John is


Look What You Made Me Do
In the days following our third date, I continued to wrestle with conflicting feelings. The result? Chaos. I became a hurricane of unpredictability. A what-will-she-do-next type of girl. We all know her. We love her, but don’t want to date her. I poked, provoked, and tried to break through his walls, demanding attention. I tried to rush things. 

I eventually came to the idea that friendship might be a better alternative. I told him via phone that I didn’t think we could meet each other’s needs. He said “OK,” but I could hear the frustration in his voice. He clearly felt blindsided. I then recited a few things I wanted, such as more communication and words of affirmation. On a granular level, I wanted him to tell me he thought I was pretty. He hadn’t yet said anything to that effect, and it bugged me. 

“Well, can you do those things?” I asked. He paused. “No,” he finally said. I wasn’t surprised. His answer only reinforced my prediction. He accused me of not knowing what I wanted. He was half-right. 

I wanted to get to know him, but I wanted him to give me more of what I needed. The atmosphere was tense. We started to argue. My phone died and prematurely ended the talk. I was mad. Then my brain turned on. He wanted me to work around him without him giving much back. This was not a game I wanted to play.

The “relationship” was effectively over. I mean, he wouldn’t even tell me that I was pretty.


In a moment of repose, I read through the last messages I sent him through clenched teeth. Sheesh, who is SHE? Gross, get out of my phone. 

If I had a do-over, would I have done things differently? 100%. I should have communicated what I was honestly feeling, instead of acting out. It probably wouldn’t have changed the outcome, but it would have saved me a lot of trouble. 

Everyone has needs when they’re dating, and they’re all legitimate, even in the uncertainty phase. Giving a partner what they need will always require some flexibility, but how and where we can bend is highly personal. 

I was initially agitated, but I now understand it really comes down to acceptance. You have to accept all of who you are and what you need. The same goes for potential partners. You can become more self-aware and communicate better, but generally speaking, we can only offer what we can offer. It’s not lost on me that if I had been more patient and allowed time for deeper feelings to develop, I might not be sitting here writing alone on a Saturday night. By the same token, as far as John goes, I still think I read it right at the outset. 

So, as it turns out, he emerged with his dignity intact. I, on the other hand, with a little help from Taylor Swift, have finally recovered from an embarrassment hangover. All in all, it was worth the lessons learned. 

A parting thought: You can’t really play the love game being closed off. We’re all scared, but you have to put yourself out there, or you’ll never get what you want. And you certainly can’t build a relationship with someone who isn’t direct with how they really feel. 

That goes for me as much as anybody.

About the Dating Coach Column

Allie Roodman is a 31-year-old millennial trying to navigate the modern dating landscape, one bad date at a time. She uses her own experiences to help others find love in her day job as a matchmaker. She is figuring it out as she goes, just like the rest of us. Connect with her on Instagram: @allieroo

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