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How I Rebuilt My Self-Esteem and Rediscovered My Sense of Self Post-Breakup by Ignoring the Experts and Creating My Own Strategy

The modern advice of taking myself on dates and cooking chicken noodle soup alone in an effort to re-learn how to love myself wasn’t going to work for me. Dating a lot of different men helped me find my way back to who I was before my traumatic breakup.

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Life after a breakup is  lonely. But it doesn't have to be.
Life after a breakup is lonely. But it doesn't have to be.

I was 25 years old, fresh out of law school, and taking on New York City. Within my first two months in the big city, I went through a horrifically traumatic breakup with a man I planned to marry.

As a compulsive law student not too long ago, I read article after article on how to recover from an overwhelming heartbreak. The modern advice experts give is to spend time alone, “become your own best friend,” and learn how to love yourself again before you even attempt to love someone else. They suggest cooking for yourself, taking yourself on date, dancing alone, and other bullshit things that I can’t actually imagine doing. Before this modern-day wisdom, the advice was, “Get back on the horse!” and find someone new. The goal of that, of course, was to push past lingering feelings for an ex and find a replacement significant other. But there’s a very large gap between these two viewpoints that nobody talks about.

I suggest a new strategy: “Get back out there!” but solely for the purpose of rediscovering the parts of yourself lost during an all-encompassing relationship and learning to love your true self again. I’m advocating for just the opposite of finding a new boyfriend or even a rebound. Dating men (preferably strangers)… a lot of them… and very different ones… can be utilized as a strategic tool to regain independence and self-esteem. Let me tell you about some of the men who helped me do just that.


MATEO.  Three weeks after my breakup – overwhelmed with loneliness and not making much progress on reconstructing my very bruised self-image – I set up my first date with Mateo. Mateo and I met in October at a dinner party. Actually, I met Mateo and his girlfriend at a dinner party in October. We both went through break ups about a month later, created dating profiles, and matched on Hinge.

Mateo’s dating profile said that he was looking for someone “open-minded.” Red flag number one. People looking for someone “open-minded” tend to want a very specific type of open-minded. In other words, they tend to be the opposite of open-minded. But I would worry about that later.

This was how I came to spend a chilly February afternoon curled up on the couch with Mateo. It was our third date, and it felt so good to have feelings for someone besides my ex. Mateo was sharing stories from his recent yoga retreat in Bali. At 6 feet and 31 years old, Mateo consistently practiced mindful meditation, swallowed plus or minus seven vitamin supplements every night, and occasionally took LSD as a growth mechanism to reset his mind and reevaluate his beliefs. In another life, Mateo would’ve been a professional surfer, with his washboard abs and chill California attitude, but in this life, he was an investor (?) or maybe an entrepreneur (?). I’m not really sure and didn’t really care, since I doubted that we had a future together that would require me to actually know. We ended our fling after another couple of dates, largely because he was too close-minded. As I predicted.

GIDEON. One week later, I was riding the subway home and spontaneously agreed to get a drink with Gideon, despite that I was dressed in a full black suit coming from court and he was just leaving the gym. My Jewish father would have liked that Gideon was Israeli. My Jewish mother would have disliked that he was 5’7”. Not genes we want to pass on to the grandkids, I could hear her saying – conveniently ignoring that my own father was the same height.

Gideon was complementary and flirtatious with both his words and body language. After a glass of wine, we went to a corner pizza shop with absolutely no heat but some warmth emanating from the coal oven. He pulled me in and kissed me on the lips right there in the pizza shop. Bold move. I respected it.

His roommate had friends over, and we decided to join them. When I left their apartment at 1 a.m., Gideon asked, “When can I see you again?” I shrugged coyly. It probably seemed like I was playing hard to get, but I really wasn’t planning on seeing him again. On my way home, my phone lit up with an image of Gideon, stripped out of his clothes (but only showcasing his bare shoulders, thank goodness) and wearing an infinitely wide, glowing smile. Draped over his naked shoulders was my favorite scarf. I gasped. Oh no, I left it at his apartment. “Guess that second date is looking less and less tentative now,” he texted flirtatiously.

That week, after reminding him three times to bring my scarf, I had my second date with Gideon. This is actually the last time, I thought. When he continued to text me every day after that, I told him it wasn’t going to work out between us. But Gideon threw a curveball: “So who am I going to take to the Backstreet Boys concert this weekend?” I melted. What woman born in the 90s could say no to the Backstreet Boys? To my surprise, the concert, plus a tour of his radio station’s studios upstairs, followed by bar hopping in the East Village, added up to one of my best New York City nights so far. Suddenly, I was in no hurry to get rid of Gideon.

That changed when he tired of goodnight kisses and requested some “romantic time alone together.” Gideon revised this text request: “Maybe intimate*.” He revised again: “To be honest, sexual*.” Is there such a thing as being too honest? I thought so.

MICHAEL. Michael looked great on paper. As a 32-year-old trader at Citibank and a former Princeton Rugby player, he was mature, professional, and seemed to have his shit together. Half Japanese, half British, and way too committed to intermittent fasting and cross-fit for his own good, he was nice to look at, too – especially with his shirt off. Only one problem: He was really boring. Trading mortgages… how does anybody actually like doing that (or talking about it)? He had zero competence in flirting, too. I didn’t think he was even interested in me until our third date when he ambushed me mid-sentence to kiss me. But once we started kissing, there was actually chemistry. Trade-offs, I suppose.

On our fourth date – for context, one week after the Backstreet Boys concert – Michael cooked me a steak dinner with grilled zucchini. Always watching his figure, there was obviously no starch served. And no dessert. And no alcohol. No music either, but that’s not the point! I showed up at Michael’s West Village apartment on my razor scooter, feeling far too immature to be dating this very adult man. After regaling me with one boring to mildly interesting story after another, we moved to the bedroom. As things heated up and shirts flew off, he asked responsibly, “Should I get a condom?” In the past, I always felt like I had to justify saying no. This time, I simply said, “Not tonight.” Conversation closed. I didn’t feel like I owed him any explanation, and I didn’t care if he approved of my answer.

Nearing 1 a.m., Michael politely offered that I could stay the night. I asked what his preference was. He told me he was “indifferent.” Indifferent… what every girl wants to hear. I was feeling pretty indifferent about him, too, but decided that I was comfortable in his king sized bed. His apartment was like a five-star hotel, decorated with exotic East Asian sculptures and immaculately clean.

In the morning, a welcomed wave of freedom rushed over me as I slid past his doorman on my scooter and exited the building. I didn’t want to see Michael again and you know what? That was okay.

DARIUS. Now in late March, with my roster nearly cleared and ready to sub out some old players for some new ones, I went on my first date with Darius. Four years past his prime days as Dartmouth’s star football player, Darius still looked around 270 pounds, and his chest was solid to the point that I imagine it’d really hurt your hand if you tried to punch him. As a former Ivy League athlete myself, I was very attracted to this part of Darius’s identity. (My college self knew exactly what numbers and what positions my favorite football players played. Darius reminded me of those happy memories.) When I told him this, he looked me in the eye and said, “Livi, don’t think of me as just part of your past. I can be part of your present, too.” Well done, Darius. Our date lasted hours – long enough for him to swallow four $17 cocktails and a $28 steak frites while I sipped one drink and picked at an appetizer.

When I got home that night, I called my mom. Who else would answer on three rings at 10:30 p.m. to rehash my date? My mom asked if I liked Darius. I paused, considering this question for the first time that night. I told her, “I had fun but I’m not sure if I really liked him.” I often enjoy first dates because I get to be whoever I want to be, and I like that girl.

That’s when I realized: I’ve been dating for me. I’ve been dating very different men because it gives me an opportunity to rediscover different parts of myself that I lost while dating my ex. And as long as I like who I am around these men and am having fun, I’ll keep seeing them. If my date likes me, great. More importantly, do I like him? And even more importantly, do I like me when I’m with him? I’m not dating right now to please anyone other than myself.


If I seem pretty badass and brimming with confidence, well good, because that’s who I’m trying to be. You see, six months ago, I was an insecure, depressed woman with a voice inside my head telling me that I was worthless. I thought the best thing about me was my boyfriend, Logan, who I suddenly was convinced was too good for me. This was despite the fact that just months ago I graduated from a top law school and landed a very competitive judicial clerkship. Logan told me he wanted me to follow my dreams, but really, he wanted me to be his mother: a stay-at-home mom and a good cook. We planned our future together, and I even agreed to raise our future family in Seattle, across the country from mine. I attended church services a few times with him and entertained the idea of raising our kids Christian. Just six months after I began dating Logan, my career, my dreams, my wishes, my values all became secondary to his. He isolated me from my friends and family. He was a master manipulator.

Visiting from medical school in Connecticut, Logan came to see me in New York to “celebrate our anniversary.” Instead of celebrating, he initiated sex, and moments later, broke up with me while still naked in my bed (the same bed that I had to and still have to sleep in every night). This was two days before a huge job interview and three days before the bar examination results were released. Logan also abandoned me during a recent escalation of some serious health issues. My heart was shattered, stomped on, spit up, and thrown out. Logan soon cut off all communication, telling me that his dad advised him to do so.

But as soon as we stopped communicating, the voice in my head telling me that I was worthless started to fade. It was suddenly so clear: The voice wasn’t my own… it was his. I had to get my own back.


I think many women can relate to putting their needs behind those of a significant other and losing touch with who they are without him. But the modern advice of spending nights in and cooking chicken noodle soup for myself in an effort to re-learn how to love myself wasn’t going to work for me.

This is partly because I’m an extrovert. When I’m feeling down, I like to be around people. But going out with friends almost made things worse after my breakup. Each friend that I saw wanted to know the details of the breakup, how I was coping with the aftermath, and, “Have you talked to him recently?!” Even worse was that my friends had watched me transform into the unhappy, sunken woman I became towards the end of my relationship with Logan. To them, I was still the person who they had seen me become. And I needed to stop seeing myself the way they now saw me.

So I developed a hypothesis: Unlike spending time with friends (or family), dating men – preferably strangers from dating apps with no preconceptions of me – would give me the opportunity to present whoever I wanted to be and rediscover the parts of myself that I used to like so much but had lost touch with. I would get dressed up, stand up straight, smile, and put my best foot forward when going out with someone new. And with enough repetition, my best foot would start to become my everyday foot. Practice creates habits, and habits become reality. Essentially, fake it until you make it.

The dates I’ve told you about have been the best therapy, because the person who showed up to those dates was me – the old me – in her true and authentic form that I had always been proud of but hadn’t seen in a very long time. Each guy allowed me to explore a different part of myself that was lost for way too long.

Mateo brought out a softer, thoughtful, spiritual side of me. Gideon brought out a spontaneous, exciting side of me. He also helped me realize that pushing and forcing things that don’t feel right is a mistake. Michael brought out a mature, professional side of me and showed me that that I can find that chemistry again after Logan. He also taught me that there’s freedom in setting boundaries. Darius taught me that if I’m enjoying my own company, and a man can facilitate that, then that’s reason enough to continue seeing him.

Right now is my time to be alone. But that doesn’t mean I shouldn’t be dating. For me, dating other men for myselfrather than to please them or make them like me – is empowering and facilitates independence. I may not be looking for love, but I’ve found something much more valuable.


Names and identifying information have been changed to protect the privacy of the individuals written about, as well as the author. Livi Strong is a pseudonym.

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