Single Mom, Dating


I could write a novel about dating as a single mom.

One day, I may. The real question is, would I file my novel under Science Fiction, or Horror? Animal Husbandry, perhaps? I have put off discussing dating time and time again because I didn’t know where to begin. Do I start at my beginning, when I became a single mom? Do I start with my first date? The first time I fell in love again, post divorce? The first time I exposed my post-baby body to someone? Let’s be honest, ok? You probably just want to read about the sex, because doesn’t everyone skip to the good parts? Oh… that’s just me? I don’t think so…

I’m not afraid to tell my truth, or to expose my sometimes sordid, frequently mundane world of dating as a single mom, but I am reluctant to use the false cloak of “expertise” to distance myself from the nitty gritty of human emotion and the clumsy ballet of courtship. I am no dating expert. Is this a surprise? I fail frequently and occasionally dramatically. At age 41, I am sensitive. My feelings get hurt easily, and I am as likely to cry from happiness as sadness. I am foolish and optimistically romantic all the way to my soft, caramel core. My friend, Jen, says that I am remarkable because she knows the million tiny rejections and occasional heartbreak I face while trying to find love, or at least a fun progression of dates. She knows the unvarnished truth, that when I am trying online dating, I will write thoughtful, funny, and insightful messages to 100 people, and will hear back from less than 10. Of those 10 responses, 3 will be politely not interested, 4 will be offers of casual sex, and 3 will be messages that excite me. Now everyone knows that I am batting a 3% average. What Jen calls remarkable though, is not my sheer tenacity and stupid persistence in the belief that romantic love is something that I will one day share with someone.

She thinks I’m remarkable because despite a nearly constant stream of rejections, I remain optimistic, I still believe I am worthy of love, I keep getting up after every hit, and I continue to get excited about a wonderful first date.

The photos in this post are all ones I have used in online dating profiles, for reference. Flattering photos, I hope, but all current and all realistic.

I have been a single mom for 5 years and 4 months. It took about a year and a half after my husband left me before I even considered dating. Before that, I was crazy with chronic sleep depravation, heartbroken, and utterly lost. Dating was the last thing on my mind, behind other seemingly fantastical activities like heli-skiing, hot-dog eating competitions, and sleeping late. If you’ve ever experienced profound grief, you know how it feels strange to hear yourself laugh again. The sounds came out, hollow and unnatural, and I panicked, wondering if my laugh always sounded robotic, like “Ha. Ha. Ha. Ha.” The first peals of laughter were rough in my chest and caught in my throat. One day though, I woke, and no tears remained to mourn the dissolution of my marriage and the excruciating absence of my stepsons. I began to long for flirting, hand-holding, and the tender beginnings of new love. In the past 4 years, of dating, I have been on roughly 25- 35 first dates. More first dates, in fact, than I experienced in my entire life, prior to having my daughter. I have met some genuinely lovely people, some incredibly lost souls, and many relationship-bruised, cautiously hopeful folks, looking to make a connection, rediscover themselves, and have fun. I hope they remember me with the same warm fondness and acceptance that color my memories of them.

Not even a month ago, I went on a date with a man who engaged my mind and heart in such a way that I didn’t for one second doubt our mutual interest and attraction.

He asked me questions that shot holes through polite small talk, and made me feel profoundly heard. I basked in his attention, and afterwards confessed to friends that when he asked if my 5 year-old daughter knows that she and I are different races, and what she thinks about race, I felt like I had truly met someone worthy of my limited time. Like all parents, particularly single parents, my free time is extremely limited and precious, and I often worry that I will never meet someone in a romantic context who is worthy of such a sacrifice. This man made me wish I had more to offer him, but at the same time made me feel like I was enough.

I realize that my singleness is one of the major differences between me and the vast majority of my friends. In many ways, our lives are so similar, punctuated by playdates, meals, trips to the pediatrician, and peppered with concerns about appropriate development and milestones. One major way we differ is that instead of cuddling with a partner to watch a movie at the end of a long day, I am trying to compose a message that makes this 41 year old mutton seem as intriguing and delightful as the 25 year old lambs who date within my age range. Come on 25 year olds… couldn’t you please leave the 35- 50 year olds to me? Just kidding… sort of. I send the first message because if I didn’t, I think I would only receive messages from people with whom I share not a single interest or commonality. I consistently receive messages from men who are 20 and more years my senior. From men who are 15- 20 years younger. From men, and women, who want me to be in a threesome with them and their regular partner. From polite men from foreign countries who would really like me to send them money via Western Union so that we can realize our deep and abiding love.

I write first because I think I still have a lot to offer the right person. My friends seem to like me, at least. Generally speaking, most people who go on dates with me like me too, at least a little. I am quite charming in person, or so I hear from my mom. But the harsh reality is that I am a stay-at-home, not particularly photogenic, 41 year old, fat mom with a little kid. I am tough and independent because every single mom must be this way.

I also never involve my daughter in my dating life, which means that I can almost never spontaneously meet someone for coffee, and overnight visits are not going to happen unless I’m in a long term, committed relationship. Even then, I’d never be able to sleep over at someone’s house, because I have to be home to take care of my daughter. I am grateful I have my darling daughter, and taking care of her is my priority, but full-time single parenting has certainly taken a toll on my dating prospects.

The date I went on a month ago was the best date I’ve had in almost 2 years. The conversation was scintillating, and 3 hours passed in an instant, with us talking, enjoying dinner, and sharing a drink and dessert. He walked me to my car and kissed me, and our teeth clinked together because we were both smiling too much and kissing too vigorously. He asked me to text him when I got home, so he’d know that I arrived safely. We planned a future date. He said that he had a lovely time with me.

Two days later, he explained in an email that we weren’t a good match, in his opinion. I was crushed, and confused.

Dating in the microcosm of the greater Burlington area in the 30- 50 year-old age range is not for the weak. Dating as a single mom is not for the weak either. At this point, I may be too self-sufficient, too bitter, or too demanding to ever find the right match. I am holding out for that special person who makes my free time worth sharing. And “hope springs eternal in the human breast…” (Alexander Pope, “An Essay on Man”) and I too will dust off my patchwork heart and hope for another date with someone who makes me bloom with optimism.


  1. Nice post @Jemima, I loved it. Dating is for everyone. No matter whether you are a teen, you are a divorcee, you are single mom, anything. There should be someone with you to share your happiness or story of distress. Thing become easier when you share you feelings to your loved one. There are online dating sites available for the baby boomers too. Dating online is one of the easiest mediums to find your significant other. But, there are frauds over the internet who are always ready to cheat the online daters. And the elderly persons easily become the prey of them as they are not that much tech-savvy. So they should consider performing a background check on their partner before moving further in the relationship.

  2. Jemima! I love this post. It is so heartfelt and real. It is human. You speak your truth, the truth and I appreciate your willingness to share yourself in such a beautiful way. Love you!

    • This post made me feel a little naked, but it’s important to me to be honest. Thank you so much for reading and for supporting me! Xoxo


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