Single Mom ISO Boyfriend: What I’ve Learned One Year Later


Single Mom ISO Boyfriend: What I’ve Learned One Year Later

“I’m perfectly fine, I live on my own.

I made up my mind, I’m better off being alone.” 

Truer words were never spoken by our Queen/Mother, Taylor Swift. 

About one year ago, I humbly commenced my dating journey post-divorce. I was completely new to the uncharted waters of apps like Bumble and Hinge. I was doe-eyed, full of wonder and hope for the future. I felt fully convinced that my life would look very different in just one calendar year. 

Yet, here I am sitting on my couch in my sweatpants, listening to Taylor Swift with my cat and eating one too many Girl Scout cookies as I anticipate spending another Valentine’s Day alone. As I survey the wreckage of the last year’s worth of dating fatalities, my biggest comfort is that I have grown and learned a lot over the course of the last 365 days. 

When I started dating, I was somewhat indiscriminate in choosing guys to go out with. I wasn’t looking for love or marriage material at first; I was merely looking for some casual dating practice. It had been a long time since I had done any sort of dating whatsoever, and I was initially going for quantity over quality. Making small talk with strangers has always given me serious social anxiety, but the more I practiced it, the better I became. I went on a lot of first dates last year. I even tried a speed dating event being held at a restaurant downtown, essentially going on 10 six-minute, back-to-back dates within the course of an hour, leaving me feeling socially exhausted at the end of the night, but proud of myself for trying something new.

I approached the field of dating with all of the studiousness and intentionality of a grad student conducting research and gathering data to write their final dissertation. I read books, I listened to podcasts, I made observations, and I compared notes with fellow students. I grew accustomed to those beginning stages (the “talking stages”) of dating, and they began to feel easier and easier. I wanted to ace them (as any good student would), and I did. But I could only go on so many dates before falling into a few actual relationships, and those taught me more about myself and the issues I still need to work on than anything. 

I learned that my tendency is to like everyone at first.

I get attached to people easily.

A few good conversations, some laughs, at least three common interests…and I start hearing wedding bells. I start imagining the distant future. But placing too much importance on someone too quickly can be dangerous. My disappointment when some sort of deal-breaker in their lifestyle or behavior eventually crops up becomes magnified when I’ve already envisioned what it would look like to spend our holidays together. I’ve learned to combat this issue in a couple of ways. When I am in “the talking stages” with someone, I’m almost always talking to multiple people at the same time. If we haven’t defined anything and aren’t exclusive yet, I am dating other people in an attempt to stay casual and not focus too much on one single person. I also get a little help from my friends. They are much better at critiquing guys and picking out red flags than I am, and they are great for pointing out potential issues that I may have been ignoring. 

I have also had the opportunity to practice healthy ways of dealing with conflict.

I have never been great at setting boundaries or communicating what I need from a partner. I often just hope that they will notice when I am uncomfortable and adjust their behavior accordingly, but it’s unfair to expect a guy to be a mind reader. I also deal with an unhealthy desire to be the “cool girl” who is chill with everything and never has any problems or issues to discuss. I worry that a guy will not like me anymore if I point out any sort of minor objection over his behavior. But throughout the last year of dating, I have found that addressing a conflict doesn’t need to send me into an anxiety spiral that leaves me hyperventilating into a brown paper bag. Many guys feel grateful when a girl is straightforward and doesn’t resort to playing petty games to get what she wants. And I have encountered so many guys who were entirely willing to work on changing something minor that bothered me because they felt like dating me was worth the effort. 

I’ve had some negative dating experiences over the past year, for sure.

Sometimes when I tell a guy that I no longer want to continue moving forward with him, he will unleash a vicious personal attack and metaphorically smash every item on the shelves before slamming the door behind him. Rather than getting caught up in the drama, I try to simply “bless and release” (as one girl in a Christian dating forum I’m a part of so aptly put it). Those situations can be really hurtful, but I try to think about what that final interaction taught me about him, and what that relationship taught me about me. No experience should be considered a waste if I was able to learn something valuable from it. 

And I am convinced that throughout the past year, I’ve been learning more about relationships and what kind of qualities I’m looking for in a partner than I could have learned from any self-help book or therapy session. 

I may be single right now. Perhaps my life doesn’t look so different on the outside than it did one year ago. But on the inside I am different, and I’m doing just fine on my own. 


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