My 25 yr old son started dating someone for the first time in his life, and what I’ve been wishing for him isn’t happening as I’d hoped.
I was excited by the idea of him dating. It made me sad he didn’t in high school, or even in college when most of his contemporaries were. It made my son sad too. He was lonely a lot, and like so many guys of his gen chose gaming to risking rejection.
I was on him constantly. ‘There’s a tech meetup in the city.’ He’s a software dev. ‘There’s a speed dating thing on EventBright.’ Of course, I was infantalizing him, but I couldn’t just sit there watching my kid waste his life away in front of a computer screen turning into an incel. I’m his mom. I love him. I had to do something to encourage him to go out, so I found networking and dating events and needled him to go.
He went out when I pushed him, so I kept pushing, but he didn’t meet anyone because he didn’t try engaging. He’d go, and then leave the event within an hour or so to say he went. ‘See! I’m going out, but I’m wasting my time and money. I feel stupid at bars or clubs and hate going to them. I feel like I’m boring and I have nothing to say. I’m going for you, Mom, so you’ll get off my back.’
But I didn’t. His sister and I helped him set up a Tinder account, which yielded even more hurt feelings when he consistently got no matches. He tried Bumble BFF, just for friends since he had none of those IRL either. Most guys who responded were gay, looking for a lover, not just friends. By his own measure, my son is heterosexual.
I don’t know the line I’m supposed to stay behind in regards to my involvement in his life. At 25, I’ve been his mom, his mentor, his closest, and only confidant. I watched him suffer through bouts of depression so dark I was afraid he’d commit suicide. My fear was so pervasive when he went black, I made a deal with him. I won’t. He can’t. ‘Till after you’re dead, Mom,’ was the only way he’d agree. Lonely is a killer, on par with heart disease and cancer.
It made me sad that my son hadn’t had a friend that lasted, no girlfriend, or sex yet. His isolation scared me. Twenty six was coming. Clinical depression often manifests in males at 26. So I kept pushing him to find friends, lovers, girlfriends — people to experience life with. And he kept getting nowhere on Tinder and at Meetups until he got on Facebook Friends and met Grace.
Recent BS in Data Science, she is 23, works half the year in Manhattan and half the year remotely for a small tech startup in New York. Born and raised in South Korea, her devout Christian family relocated here when Grace was 10. I’ve raised both my kids without religion and to value character over culture. Kindness is what they should seek and treasure. And a safe harbor when together.
They began a friendship with Grace’s invites to parties and tech events to attend together. At most of them she was on her phone, or taking selfies for her socials. When she went back to Manhattan, they spoke on the phone often, for hours, mostly about her life, her many health issues, her job. She asked him few questions, didn’t really engage with his responses, often putting him down for what she felt was his lack of ambition in business, and in becoming a master musician. My son plays the guitar, sax, and piano well, but for enjoyment. Grace made it clear she considered him weak whenever he cried. She expected attention, encouragement, empathy, but gave none.
To say my son was desperate for connection would be understating his psyche’s need to associate with people other than me and his sister. His relationship with his father is fraught and he doesn’t feel comfortable being vulnerable with his dad. While he complained to me about Grace’s hurtful behavior often, she was all he had, so he kept talking to her, and hanging out with her when she was in town.
Six months into their friendship, and coming up on the holidays (when being single particularly sucks), Grace began to hint to my son she was looking for more. She stroked him, telling him he was cute, smart, witty. She became a lot more touchy — squeezing his arm or his hand kind of thing, my son relayed to me one evening in early December.
‘I don’t know what to do, Mom,’ he said. ‘I don’t wanta wreck our friendship cuz I like a lot about Grace — she’s smart, educated, ambitious, a math-head. But I don’t think I want to get into a romantic relationship with her.’
My heart sank. This girl was clearly interested in more with my son and he was rejecting her. He was blowing an opportunity to experience an intimate relationship without exploring the possibility that Grace simply didn’t know what he needed/wanted, and if he clued her in she may indeed be responsive. I asked him many questions about their interactions and listened to his misgivings. I suggested he voice his frustrations with her hurtful behavior. If Grace really wanted to be intimate, she’d acknowledge his trepidation and at least try to be less critical, and distracted, and show more interest in him.
Days later my son and Grace were officially a couple. He told me she’d agreed to put her phone away, and did, right before she kissed him…
And I’d love to say this story is happily ever after, but not so much.
It’s been over a month since their coupling. My son is stressed all the time. He literally passed out, the only time in his entire life, when she was at him for not playing the piano to her standards a couple weeks back. He had a bruise on his forehead and headaches for days. They spent New Year’s Eve together and consummated their boyfriend/girlfriend status, but their sex has been rather fraught. Being called “Daddy” doesn’t really work for him.
He talks to me about his relationship with Grace without my prompting because I raised my kids to freely express their feelings and thoughts to me throughout their lives with my solemn oath not to reprimand or judge them with their disclosures. It’s a hard promise to keep sometimes, but I guess for the most part I have because they trust me enough to confide in me. Again, I don’t know the line moms and sons are not supposed to cross in our communication. I’m still his most trusted confidant. I was hoping a girlfriend would take on at least part of that role, but Grace hasn’t.
The last couple of days he’s been asking me if he should break up with her. Dating eight weeks now, he’s falling behind in his Master’s program, he’s exhausted, anxious, tense a lot. Of course, I could not tell him what to do so I threw his question back at him.
‘You’re a math guy,’ I started. He nodded. ‘What percent of your time together would you say you’ve had fun with Grace?’
He thought about it a minute, then went through a couple fun dates and events he’d taken her to, since when they became a couple, my son’s been paying for everything they do. Then he added, ‘Maybe 20% has been fun with her. The rest has been pretty stressful. I get why you’re crazy now.’
He was referring to my 29 yr marriage to his father. Ouch. ‘Do what I’ve said, not what I’ve done,’ but I knew it was crap as it left my mouth.
‘Bullshit.’ He said it like dropping a bomb. ‘Kids do what we see.’
‘Yeah. I know,’ I admitted, guilt suffocating me. ‘I’m sorry your dad and I have had so much discord. I’m sorry I modeled staying with someone who objectified me.’
Like Grace does me. I really think she’s looking for a daddy figure. I want a partner, someone who’s a safe harbor, like I’ve been trying to be for her. He flashed a half-grin like ‘Surprise! I was listening.’
‘Touche,’ I said smiling back at him. And for a second I feel that electric connection between us. I don’t trust my parenting that I’ve set my kids up to take care of themselves better than I’ve taken care of me. And I want so much more for them in their relationships than to become filled with contempt. The best I can tell ya honey, is communicate. Tell Grace how you feel and why. Listen to her too. Maybe you two can still forge a path together. And maybe not.’
‘I get it. I just wanta feel like both of us are doing the 4 Steps.’ He grinned again.
I did too.
‘Gotta get back,’ he said, and got up from the table. ‘Thanks, Mom.’ Then he kissed the top of my head and left the kitchen.
The 4 Steps to Better Relationships (to which my son was referring):
- We are a TEAM.
- What does my partner need/want?
- What do I need/want?
- Compromise.

