IT HAPPENED TO ME: I'm Online Dating With My Mother (And She's Better At It Than Me)

Welcome to the nausea-inducing world of online dating at the same time your mother.

May 5, 2014 at 3:00pm | Leave a comment

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“I got drunk for the first time since college last night,” my mother tells me as she recounts her date from the night before with a man she’d met online. “We were out dancing until midnight and I wore that new little blue dress with the cheerleader skirt, and when I went to the bathroom, he finished my drink so that I wouldn’t argue about leaving. When he left my place, I was too woozy to walk him to the door, but I did manage to get myself to the bathroom to throw up before going to sleep. I definitely felt better after that.” 
 
Welcome to the nausea-inducing world of online dating at the same time your mother. When my father died two years ago, dating was the last thing on my mind. I was in a committed, long-distance relationship with a man who three months later would become my fiancé, and was also committed to supporting my mother, who was grieving the loss of the man she’d been married to for 43 years. 
 
After a year of mourning, my mother asked a friend to take some new photos of her and suddenly, she was on three dating sites and calling me every time a new man would look at her profile. My phone’s battery started running low almost immediately.
 
This is a phenomenon so many others in my generation are experiencing: Our parents re-enter the dating pool after decades without practice and we have to hear all the dirty details. Though people over 50 are the fastest growing population on online dating sites, I wasn’t expecting my technologically challenged mother to so successfully navigate the “flirts” and “likes”, or to enjoy herself so much. After all, this is the woman who’s tested my patience while asking where to click to view photos on Facebook.
 
As her guide into the world of online dating, I advised her on what to watch out for: Don’t write too much back and forth with someone before meeting them; some people will be rude/reveal too much/not ask questions; and most of the men in her age group would not look like their photos.
 
Despite my warnings, she was giddy with all the interest, with feeling desired and told she was beautiful, and though by now I was immersed in the grief of a freshly broken-off engagement, I was happy to hear excitement and hope in her voice rather than pain and despair. That is, until I realized that we were competing for men, at least online.
 
My mom lives in North Carolina and I live in Brooklyn, and somehow, even though I advised her to limit her desired geographical and age range, she has been receiving messages from men of all ages, all over the country. She has been trolled by men as young as 35, who she’s convinced see her just as a wealthy widow (only one of the w’s applies there).
 
Once, in an attempt to make a shidduch, she even forwarded me a message she received on JDate from a man in his early 40s who lives in New York, writing “Not for me, but maybe for you?"
 
Obviously I wasn’t about to take my mother’s rejects. But I did take her advice, which was to wait for the passing of a full season after my break-up before putting myself back on the market. (I also maxed out the insurance that paid for the therapists who were getting me through it.)
 
When that time rolled around, my roommate came home from work and told me that she and her co-workers had just discovered a new online dating app called Tinder.
 
Despite my reluctance to reenter the world of online dating, my roommate showed me how the app worked: you view photos of potential matches and swipe to the left if you don’t find the person attractive, or swipe to the right if you do. No lists of hobbies, skills, favorite movies -- you're being judged solely on how photogenic you are. For once I envied my mother -- the older online dating generation is a bit more lenient with physical appearance. She says they are mainly looking for someone self-sufficient without too many health issues.
 
My first Tinder date was set up within about an hour of adding my profile, and it was for that very night. Since my date knew where I was, he suggested a nearby bar, and 20 minutes later I was awaiting my first online date in years. 
 
While the typical first Tinder date involves meeting at a bar and seeing where the night takes you, my mom was being taken out to sober lunches or meetings over coffee. One guy I went out with was only two glasses of wine in when he decided to tell me about the wild women he’d already met on Tinder. When his stories approached the end of the evenings, he would say, “I’m not going to say what happened next because I want to be discreet,” as if telling me he had sex with them would ruin his chances with me. 
 
Based on my own dating experiences, my mother had expected to guard her “virtue” on first dates, only to discover that men her age were more eager to go to bed alone (and early) than with their dates. Affection, compatibility, and good conversation are replacing sex for seniors, which my mom says is not a bad thing.
 
She does seem to derive special conspiratorial glee from comparing notes about the guys we’re meeting. Recently she asked if one I’d gone out with a few nights earlier was attractive. “Yes, he’s cute, but I don’t want to rip his clothes off or anything,” I told her. To which she replied, “Well then he’s not for you. You need to feel the attraction -– that’s just the best feeling.” When I told her recently that I want to find someone playful and flirtatious to keep the chemistry exciting, she reminded me, “If he plays and flirts like that with you, he’ll be playing with a lot of other women too.” I might know more about sex, but she still knows more about commitment.
 
After 43 years with the same man, being physically or emotionally vulnerable with another one is a huge leap, but it’s one she seems ready to take. And here I am, 35-years-old and wondering if I’ll ever be ready to get married.
 
Since she’s not interested in getting remarried, my mom doesn’t have to worry about being criticized for not loading the dishwasher properly (“back to front, silverware top down”), keeping the house clean enough, starting a family, sharing a bank account, and surviving a midlife crisis. She’s just looking for someone to have fun with. And while that is all well and good, it can be difficult for her to allow herself to continue getting close with someone who might, even at 70, be unable to commit. Aren’t men supposed to grow up eventually? 
 
When I started dating in my early adolescence my mom would tell me, “The secret is to be mysterious.” After breaking off my engagement, I spent months in therapy learning how to break free from the being “the pleaser,” and to express what I want when I want it, to say how I feel when I’m feeling it. Being mysterious at this point sounds like it would lead to a lot of miscommunication. I want to be direct and upfront, which is really what Tinder does best: cutting to the chase. So now the advice I give back to my mother is to be direct and to say what you want. And it’s worked for her: She beat me to finding a man. 
 
I want to believe that her success is the result of facing lower stakes than mine, and having lower expectations. But given how few eligible men her age want to date their contemporaries, the fact that she found someone local who makes her feel like a high-schooler in love is pretty remarkable. 
 
These days, my mom asks less for my dating advice and more about how my romantic life is going. And sometimes it’s difficult to be the kid in our relationship again, the one who doesn’t know the answers. But in an important way, I’m happy my mom is still there for me as a role model; seeing how she overcame heartbreak and loss to find someone she genuinely wants to share her time with restores my hope that I’ll also find someone to click.