10 Crucial Lessons I Learned About Dating From My Mom


When my dad passed away almost two years ago, my fifty-something mom and I both found ourselves single in Manhattan. The amazing thing about someone whose been out of the game for 30 years, is that she has no knowledge or willingness to participate in the calculated dance that is current urban dating. Instead, she’s made her own way. And she’s fucking killing it.

Here are ten things I learned about dating from my rad mom who’s getting back into the game:

1. Cool is the rule – a platitude she actually says to me and to my friends to the point that we are now saying it to each other. Effective parenting? Just be cool – and not in a “Gillian Flynn’s cool girl” way. Be cool by living your life, honoring your own plans, and if a boy doesn’t seem into you he probably isn’t. Your time is another’s – and your own – privilege. Don’t forget it.

2. You don’t need to tell your friends about every first-ish date. Anyone that my mother ultimately decides is awesome enough to meet my younger sister and me has to be a certain qualifying level of fantastic and familiar. Getting rid of the obligatory feeling to share takes some of the pressure off so you can just be in it. When you’re ready to share, you’ll know. *Ed note – we haven’t met anyone yet.

3. White Lies Bite You Later – My mom lives unapologetically – if she doesn’t like a food she’ll come out and suggest a different cuisine du jour. It’s okay to let him pick, but it’s also okay to say that you don’t like oysters and suggest sushi instead. Chances are that if he sticks around, you’ll be outed anyway.

4. Dating is harder when you’re broken. When real shit happens in your life you may not want to share it with a partner for a while. That is No need to apologize for doing you and not necessarily even wanting a partner in the first place. My mom, a beacon of feminism and fabulousness, lives without any apology whatsoever. And yes, I’m obsessed with her.

5. Be true to your shallow side, but embrace openness. My mom has compromised on the bald-esque (my dad had a full head of hair) but under 5’10 will never fly for her. Ever. At 5’9, she feels clunky and unsexy next to a guy her height or shorter. Though she tried once or twice, she knows this. And she owns this. Superficial? Sure. But facts are facts.

6. Abide by the undergarment litmus test: If you can put a pencil underneath your boobs and it stays there, you need to wear a bra with that dress. It’s physics. Or something.

7. Be Present: When you’re on the date, actually be on the date. Once you decide to go, actively listen, and give the person the opportunity to wow you (or bore you, underwhelm you…or wow you!). You can journal about it and psychoanalyze the shit out of it with your friends later, but innocent until proven guilty. Sound baby boomer advice for basically all facets of our lives.

8. Exes Inform: My mom’s thirty year relationship with my dad can hardly be compared to my relationships with my high school and college boyfriends. Even still, we should choose not to be haunted by our past relationships – both for the good and the bad – but use them to inform our future ones. No one will ever replace my dad, but no one should, and that’s okay. By being up front and acknowledging them, to ourselves and our future partners (to an extent) we carry the knowledge with us and can best serve our current needs.

9. Always Be The Best You: Millennial App dating sometimes feels like a contest of who gives less of a shit. Screw that! Always be you, and the best version of you. “You never know – he could set you up with a friend, become a colleague, be your future husband’s brother!” Always be on.
9a. Always look decent at airports because every time I’ve looked hideous, I’ve inevitably run into someone I know. I hate it when she’s right.

10. Laugh.
Laugh at how totally weird life is and how silly dating can feel. We laugh at the absurdity of it all.

This is an actual text conversation between Sam, a relatively new, though instant close friend, and my mommy.