My Son And I Are Simultaneously Dating My Boyfriend

A divorced mom takes on the tricky situation of introducing her son to her boyfriend.

My Son And I Are Simultaneously Dating My Boyfriend 4 PM production / Shutterstock

Dating with a kid isn't always easy. I waited five months before introducing my boyfriend, Andy, to my 3-year-old son. All the books and advice givers, including my therapist, suggested we meet at a public place; I chose the Children's Museum of Manhattan and invited my mother to come along as a buffer.

Up to that point, Andy and I spent every weekend exploring each other's bodies and temperaments, talking endlessly into the night as you do when you're first dating. Conversations never seemed to falter; our want for each other was constant. After a difficult divorce, the attention made me feel alive again and I cherished it.


Logically, as Andy and I got closer, I wanted him to meet Jake. He was a wonderful man, a teacher by profession, and a great listener, and made me laugh. But would my son like him? This was the big question.

Andy made his first move at the Dora the Explorer exhibit by tossing Jake a few soft shapes to play with. Jake looked up, batted his big brown eyes, and pocketed the toys.

"Say 'thank you' to Andy," I said to Jake. But Jake played it coy. He shook his head, got loose from my hold, and tackled a wall of blue blocks.

RELATED: I'm The Single Mom Of 7 Kids (And It's The Happiest I've Ever Been)

Andy laughed and told me not to worry, but I analyzed the situation. Would Andy think Jake was as perfect as I did?


Jake had just turned three. He was a sweet kid, affectionate and kind — but perfect manners? Who was I kidding? My mother reminded me that my goal for the day — for Jake to make eye contact and indicate some sort of recognition of Andy — had been accomplished.

Our next date was at the American Museum of Natural History. It had been raining all morning and Jake was full of energy. He wanted to climb the Brachiosaurus in the main lobby, was determined to torture the creatures in the lizard exhibit, and demanded a bag of goldfish right now, right now, right now.

Andy was unflappable. He stood in line to buy tickets, lifted a thrilled Jake on his shoulders, diverted him from wrecking the Stegosaurus skeleton, and hailed a cab in the downpour so that we didn't have to walk to the parking garage.

I looked over at Andy's strained face as he stood in the rain. He winced each time a cab passed him and as his clothes continued to get soaked. I wondered if we'd make it to the third date.


Jake fell asleep on the car ride home, and I took a quiet moment, to be frank with Andy. I was having a hard time mixing mother and lover, and I imagined he was as well. We'd exchanged cuddling and kissing for chasing Jake around a cavernous room of African mammals.

"You can never really be ready for how a kid is going to act, especially in a new situation like this... you know... Mommy's new friend," I said.

Andy paused. "What if I wasn't ready to meet Jake?" Wasn't ready to meet Jake? I thought the whole point of our outings was because Andy was ready. The question made me defensive and protective.

"Our relationship wouldn't have gone further if you weren't ready to spend time with my child," I said. He nodded and said he had fun when I dropped him off at his apartment. Yet, I felt uneasy.


"How was the museum?" a divorced friend with a son from his previous marriage, and two from his current marriage, asked.

"Andy saw me in full Mom mode. I think it was strange for both of us."

"He's going from zero to sixty," my friend said. "You're the woman he's sleeping with. Now he's watching you wipe your child in the bathroom. It's going to take some time."

A few days later Andy came over to the house for dinner and seemed unfazed by my repeated requests for Jake to sit down. He even complimented my entertaining tactics for getting him to eat. Maybe he's getting used to us, I thought.

When bedtime came, Andy offered to read The Jungle Book on the couch, and my son nuzzled between Andy's legs. In a moment that should have been comforting and sentimental the worse possible scenario occurred to me. What if Jake got close to Andy, and then we split up?


Andy came over early in the day on our fourth date. This time, I played with my son more than I ever had. I was Supermom. I wrestled him, chased him, crawled through a plastic tunnel, and shot basketball hoops. I expected Andy to do the same. And he did, but it wasn't quite enough.

RELATED: A Dad Asks His Mom To Watch His Kid For Free On Week Days — She Says No Even Though He Pays Her Rent

I wondered if he was genuinely having a good time or pretending for my sake. Was Andy living up to my expectations?

Later, I put in Jake's favorite movie, Lady and the Tramp II. Andy nodded out on the couch while Jake watched enthusiastically. It should have been my cue to let things settle. We had just spent four hours entertaining my child. Instead, I pushed. As bizarre as it seemed, I wanted Andy to be involved in every aspect of our time together—even if it was watching a mind-numbing children's movie.


"Andy, don't you want to watch the movie?" I asked.

"I need to relax for a bit," he said and closed his eyes.

Midway through the movie, Jake shook Andy's arm.

"Do you want to color, Andy?"

"Not right now," Andy said, gently, his eyes still closed.

"I'll color with you, honey," I said. After forty-five minutes of stenciling triangles and squares, I ushered him to his room. "Say good night to Andy."

"Good night, Andy," he said.

"Good night," Andy meekly responded.

His lackluster "good night" threw me off. Was Andy blowing off my child?

"What's my role here?" Andy asked when I came down.

"There is no role. I just want you to be crazy about my son," I said. "So when my child says good night to you, I want you to enthusiastically say goodnight."


"I said good night!"

"No, you said 'good night.' Not 'GOOD NIGHT!'"

"Look," he said, "I know this is going to sound like I'm jealous of Jake, but you ignore me when it's the three of us. I'm trying to figure it out."

RELATED: A Mom Whose Son Wasn't Invited To A Birthday Party Calls Other Parent & Is Told Exactly Why He Was Excluded

I was so eager to judge Andy and his ability to connect with my child, I didn't consider my behavior. I was trying to direct a relationship instead of allowing it to happen organically between the two of them.

I realized that when Andy was with Jake and me, I didn't actually want him to be himself. I wanted him to be a perpetual clown, the man who would be a perfect figure in my son's life, someone Jake would play football with and be inspired by, someone who would never get tired — of course, a completely unrealistic expectation.


"I'm not sure why Andy's willing to be on trial, but he is," my therapist said once I relayed the story. "Why are you expecting him not to be good with your son?"

"I want him to be enthusiastic," I said. "All the time. I want my son to like him."

"If you start telling Andy how to act, you're going to do exactly the opposite of what you want," she said. "Besides, it doesn't sound like he did anything offensive."

She was right.

"As the mother, you set the tone," my therapist instructed. "If you want your son and Andy to be comfortable, then you have to be comfortable. If you want Andy to be himself, then you have to be yourself."

When I talked to Andy that night after therapy, I confessed. "I was hard on you the last time you were over."


"I could have been a little more communicative about how I was feeling," he said. "Next time, I'll be more enthusiastic about my good nights. I'm sorry."

A few nights later, Andy came over about half an hour before Jake's bedtime. We talked and did a puzzle, then Andy read a story about a beaver having trouble making a dam.

We were both more relaxed, made fun of the troubled beaver, and I even went into the other room to get Jake a cup of milk without neurotically checking on them. With his pajamas on, Jake snuggled between me and Andy on the couch and we listened to Andy read the story.

When it was time to say good night, Andy gave Jake a high five.


Upstairs, I tucked Jake, his zebra, elephant, and dinosaur under the covers.

"Did you have a nice time tonight, honey?" I asked.

"Yes," Jake said. "With Andy."

I went downstairs after Jake fell asleep and curled up with Andy on the couch. "He likes you," I said.

"Good, because I like him too," Andy said.

And there we were, the three of us, enjoying our new relationship.

RELATED: TikToker Exposes The Reality Of Dating As A Single Mom & The Audacity Of Men Who Shame Her

Hayley Krischer is an award-winning journalist who has written for The New York Times, The New York Times Magazine, The Atlantic, Marie Claire, Elle, and more.

YourTango may earn an affiliate commission if you buy something through links featured in this article.