Navigating the dating world as a single mother has its unique challenges, but one of the most eye-opening realizations I’ve had is how many men out there aren’t looking for a girlfriend or wife—they’re looking for a mom. I’ve seen it over and over again, and the behavior is so glaring that it’s impossible to ignore. After a date, I even brought it up with my therapist, who confirmed my suspicion: many of these men are trying to heal a “mom wound,” whether they realize it or not.
Let me walk you through one of these experiences—a date that, in hindsight, felt more like a babysitting gig.
It started when I made plans with this man (if I can even call him that). I told him I’d be getting out of work late and wouldn’t have time to orchestrate an elaborate plan for the evening. He assured me that was fine and he’d handle it. Great, I thought—someone who’s proactive! Or so I thought.
When I got off work, I called him: “Hi! Where am I meeting you?” His response? “Oh, I don’t know—what did you want to do?” I was already mega annoyed. I’d explicitly said I didn’t have the bandwidth to plan, and yet here we were, with me doing exactly that, after a long day at work. Frustrated, I suggested grabbing smoothies in Chinatown. He said, “Perfect, I’ll see you at my place.”
I arrive at his place, and to my surprise, he immediately hops into my car without even asking if I wanted to drive. Now, let me be clear: I don’t mind driving, but the assumption? The entitlement? Red flag number two.
We get to Chinatown, I pay to park my car (red flag three), and we head to the smoothie place. At the register, we both pull out our cards at the same time, like a duel. He then quickly retracts his card and says, “Thank you!”—leaving me to cover the bill. Even the cashier looked at him sideways. It is not about how much the smoothies cost, ($9--blame inflation), but about the principle. If you don't have $9 to cover smoothies, why are you out on a date?
The rest of the date wasn’t much better. He asked, “Where should we go next?” I decided on a nearby park with a nice view of the Chicago skyline. I led the walk, the conversation, and every decision about where to sit and when to leave. By the end of the night, I was exhausted—not from the date itself, but from doing all the emotional and logistical labor.
As I dropped him off, he had the audacity to expect me to come upstairs with him. I declined, of course, but the whole experience left me drained. When I recounted the date to my therapist, she asked me a question that hit me hard:
“How did that make you feel any different than being with your 8-year-old son?”
The truth? It didn’t. I realized I’d spent the entire evening mothering this man. From making plans to leading the outing to footing the bill, I wasn’t on a date—I was managing someone else’s needs, just like I do for my child.
But here’s the difference: my son is eight. He’s supposed to need me in that way. Grown men? Not so much.
This isn’t just about bad manners or a lack of initiative. It’s about a deeper issue that many men are dealing with—a need for nurturing, guidance, and care that stems from unresolved wounds with their own mothers. I don’t blame them for having those wounds, but I’m not here to be their therapist or fill a parental role in their lives.
Dating is supposed to be about partnership, not parenting. I’ve learned to set boundaries and recognize the signs early on. If a man can’t show up as an equal—emotionally, mentally, and practically—then he’s not for me.
Because at the end of the day, I already have one child to raise. I’m not signing up for another.
love,
alejandra