I’m 37, single, and it’s all my mom’s fault! She’s made my life a HELL! I was sick of her over-the-top “care,” but the worst part? She ruined my love life. She scared off EVERY single guy I ever dated. None of them were ever “good enough.” But then Theo came along. I felt it — he was the one. So, I didn’t want my mom to find out.

I invited Theo over. Candles, wine, pie — it was perfect. We were talking, getting closer… when suddenly, I heard someone SNEEZE. No. Way. I open the closet — and there she is. My MOM! I was horrified. Furious.

“I had to see him for myself,” she says and then hands him a piece of paper. Theo loo

When he left, my heart was in pieces. I was sure I’d never see him again. But days later, there’s a knock on the door. I open it and see Theo with flowers! God, if only I knew that moment wouldn’t last long…

Me: “So where are we going, honey?”

Theo: “I need to tell you something… Uh… would you mind if I asked YOUR MOM out on a date?”

I swear, I almost fainted right then and there. A date? With my mother? My first reaction was a mixture of shock, confusion, and—honestly—some jealousy. It made zero sense! But Theo was standing there, looking completely serious.

“Wait,” I managed to say after a few seconds of awkward silence, “why would you want to date her? Are you out of your mind?”

He hesitated. “Look, I know it sounds crazy. But I realized your mom isn’t going to let us be happy unless she’s convinced that I’m the real deal. And… she’s made it very clear that she doesn’t trust me yet.” He shrugged, looking a bit embarrassed. “I’m not actually interested in your mom romantically. But sometimes you have to show people who you really are on their own terms. So, I thought… if she wants to get to know me that badly, maybe taking her on one official date would help.”

I didn’t know if I should roll my eyes or burst into tears. On one hand, it was oddly sweet that he’d do something so dramatic just to win Mom’s favor. On the other hand, the image of them sitting in a candlelit restaurant made me feel physically ill. Yet I couldn’t ignore the truth: Mom had driven away every single guy I’d ever brought home. Theo was the only man who ever tried to get on her good side rather than run.

For the next hour, we talked it through. I demanded some boundaries—like no kissing, obviously. Theo just laughed and promised he wasn’t aiming for anything romantic. He was determined to show my mother he was a genuine, respectful person who wouldn’t hurt her precious daughter. With a knot in my stomach, I finally sighed and relented.

So, two nights later, there I was in a weird situation: I helped Theo pick out flowers for my own mother. Then he left to pick her up while I stayed home, pacing around and wondering if I’d lost my mind. My best friend, Rina, texted me nonstop: “This is insane!” and “Girl, you better be sure he’s worth it!” I wasn’t entirely sure, but I had to trust my gut.

ks at me, confused. I grab the note, read it, and just freeze from embarrassment. “RULES FOR DATING MY DAUGHTER?!”

Me: “Mom, are you insane?!”

Theo: “I… I think I should go.”

An hour into their “date,” I tried to distract myself with a movie, but I just kept checking my phone. What were they talking about? Was Mom laying into him with her usual jabs, or was she actually being… nice? My phone finally buzzed. It was Theo:

Theo (Text): Your mom insisted on driving us to some retro diner. We’re actually having a decent time. She’s telling me about your childhood. She’s pretty funny when she’s not, you know, hiding in closets…

Funny? My mother? I was perplexed. Then I got another text:

Theo (Text): Don’t worry, we’re sticking to the ground rules. This is all for you. I promise.

I felt a tiny bit of relief. But that relief was shattered later that night when I got a frantic call from Mom.

Her voice came through in a panic: “The car’s got a flat tire, and we’re on a deserted road outside town!” My heart lurched. I asked if everything was okay, if they needed me to call a tow truck, but then Mom’s tone shifted. She sounded more exasperated than worried.

“I’m not helpless, you know,” she huffed. “We’re fine. Just letting you know we’ll be late getting home.”

Late? Getting home from a date with Theo? My mind flipped all sorts of scenarios. To calm myself, I remembered Theo’s sincerity and how he was just doing this to get in Mom’s good graces. Still, it felt awkward. They ended up waiting for a roadside assistance guy for almost two hours. When they finally pulled into our driveway, I was on the porch, arms folded, adrenaline pumping.

“Glad you’re home safe,” I said stiffly.

Mom groaned as she got out of the car. “I told you we’d be fine. Theo even tried to change the tire himself, but there was a problem with the lug nuts, and we had to get a professional.” She paused and looked over at Theo with something resembling… approval?

Theo got out, shrugged, and managed a smile. “Your mom can be pretty resourceful,” he said. “She managed to find a spare phone charger in the trunk and everything.”

Great. Now they were bonding over roadside emergencies. I tried not to let my jealousy show, but I must have looked tense..