From Playdates to First Dates: Dating as a 30+ Single Mom
My top tips, what I wear, and the surprising things I’ve learned along the way
The Second Act is a weekly newsletter packed with obsessively-curated recommendations and ideas—let’s get to it!
📚 This is a Love Story by Jessica Soffer: I was immediately hooked by this novel but like many of the stories at its heart, that initial spark only deepened. I kept finding myself thinking, “Oh, I see what she’s doing here,” then being completely floored by the direction. Take, for example, the vignettes of love in Central Park that morph into the touchpoint storyline of Abe recounting memories for his dying wife Jane, which then shifts into several chapters told from the perspective of a student once infatuated with Abe. To borrow a sentence from Soffer on early love, “It makes everything lift.” Trust me on this one!
🎥 Bridget Jones: Mad About the Boy: Bridget Jones finally has some luck in her life; she has a great job as a screenwriter, her family and a new boyfriend; the fact that he is over twenty years younger than her isn't the only thing that is causing problems. I watched this with some girl friends on Valentines day and it was soooo cute. We all gigled and loved it!
📺 The SNL 50: Beyond Saturday Night docu-series on Peacock. (No, not the Questlove one about the show’s musical impact, but that’s on my list, too). I really enjoyed the first episode of this four-part series about the audition process, but I was feral for the third episode all about the writers. The episode goes through the making of an episode (in this case, one from last year hosted by Ayo Edebiri) in minute detail. I was riveted. If you’re a writer or a fan of the show or a fan of Romantic Comedy by Curtis Sittenfeld, this is a must-see!
One of the most frequently asked questions I’ve gotten in the past year is “Are you dating?”
The answer is, Yes!!! As for the “who, what, when and how” of it all I may not be ready to share with you yet, but what I can share are some tips and fun tidbits I’ve gathered along the way.
Never did I ever imagine writing the words that I am dating in my 30s as a single mom of two. Between FaceTiming with my besties sorting out date night outfits (see the bottom of this newsletter) to coming up with fun nicknames for different people, my friends never call a guy by his first name) it’s been quite fun getting back in to the swing of things after taking a near 13 year hiatus from single life.
In the beginning, I’ll admit, I had some insecurities when stepping back into the dating world. I found myself hesitant—almost shy—about sharing that I had kids and, dare I even say it, that I had dissolved my marriage. It felt like wearing a neon sign that screamed “Baggage Alert!” I worried about being judged or, worse, rejected. Putting myself out there after years of routine and familiarity was nerve-wracking, to say the least.
And then came the “firsts”—a tidal wave of them. The first awkward date where I overthought every word I said, the first ghosting that hit me harder than I’d like to admit, the first butterflies that took me completely by surprise (because who knew I’d feel those again?). Each moment, whether amazing or uncomfortable, was a step toward rediscovering pieces of myself I’d tucked away for years.
The best part? The sting of rejection we all felt in our 20s doesn’t hit nearly as hard in our 30s. I’m a much more evolved and secure version of myself now, and I don’t take it personally if things don’t work out. Instead of seeing it as a reflection of my worth, I view it as a filter for finding someone who truly fits into my life.
Through it all, I’ve come to see dating not as a daunting chore, but as a beautiful opportunity to reconnect with who I am beyond being a mom or an ex. I’ve learned to embrace my own wants and needs without apology, to relish the thrill of new connections, and to find joy in the unexpected.
This is the reality of dating —the good, the bad, and all the in-between moments that remind you that starting over might feel terrifying at first, but it’s also where some of life’s most rewarding surprises lie waiting.
I’m off the the apps because I am dating someone special, who I can now share is my boyrfriend. And yes, I know that is vague—trust me, I am eye rolling with you. I’ll just say, it’s probably not the love story you were expecting. But, things feel fresh, exciting, and… dare I say, a little magical? I’ll share more when I’m ready as I tend to do.
Schedule Like a Boss: Your calendar is sacred. If he can’t plan ahead or respect your Tuesday PTA meeting, he’s not ready for your level of organization. If I am planning to go on a date with someone that is exactly what it is - a plan. So if the guy can’t make a plan and put it on ink, he isn’t worth dating in my book.
Be Wary of the “Too Cool” Dad: If his profile mentions “adventurer” and his photos are all shirtless hiking pics, you’re not dating him—you’re adopting his midlife crisis.
Skip the Resume Reading: You’re not interviewing him for a job, so don’t waste time on his LinkedIn accomplishments. What you really want to know is: Can he sit through a kids' movie without complaining?
Your Gut Is Never Wrong: That tiny voice saying, “This guy feels like a walking red flag”? Listen to her.
Step Outside Your “Type”: Your “type” might feel like a safe bet, but it’s often rooted in old patterns that no longer serve you. Be open to dating someone who surprises you—whether it’s their career, style, or interests. Growth often happens when we step outside our comfort zones, and you might discover a deeper connection with someone completely unexpected. It’s not about settling; it’s about expanding your perspective.
Take the Lead: When it comes to my kids, I will only date someone who truly lets me take the lead. In terms of my time with my kids, me talking on the phone around my kids, having anyone meet my kids, etc… (to be clear, I have not introduced my children to anyone I have dated.) I think it’s very important for men to let the mom take the lead on what makes her feel the most comfortable.
Okay so what are we wearing? For the first date I tend to wear something like the below. A pair of good fitting jeans with a sweater or cardigan, low heel and perhaps a little lace popping out. Fun fact, I tend to wear the same thing on every first date (unless a specific attire is required) It may sound boring, but it helps my nervous jitters to not have to stress about this part. I may switch up the shoes or accessories but having a staple fit that I’m confortable in is a relief! On the second/third date I like to dress up slightly more which you will find a few inspirations of below.
Outfit Inspiration:
Let me know if you want links to anything!
The Second Act is an entirely reader-supported publication. Click here to subscribe or gift a friend a subscription here (if a friend sent you this —tell them thanks!). Anything you want covered? Questions? Reply with a comment below!