Why sometimes you should text him even when you think you shouldn’t


A couple months ago I was driving upstate New York to a town a 1.5 hours away from my home in New York City, catching up on my podcasts. While cruising through the foothills of the Catskill mountains, NPR’s Anna Sale told a touching love story on This American Life about herself — a New York City journalist (um, like this writer) — and her boyfriend, an ecologist. Listen here, it’s so good:

It was a fantastic tale, but more critically, an eerie coincidence. A month prior I’d messaged with a sexy ecologist who lived more or less near my day’s destination, and scored a 95% match on OKCupid. I’d been excited about the Korean BBQ date we’d planned, but at the last minute he canceled, blaming a springtime cold, and failed to follow up. It was clear I’d been blown off. Boo hoo. Back to swiping dudes online!

But this coincidence of happening upon the journalist/ecologist love story on the day when I was in the neighborhood of an ecologist love interest was just too much. Certainly it was a sign to make a move, right? What did I have to lose (except the very high risk of being force-fed a giant slice of humble pie a la mode)? So, with a lurch in my gut, I found his contact info was still in my iPhone and sent this message:

Hi! This is Emma. I am driving to New Paltz on business and just listened to a sweet This American Life story about a journalist and an ecologist, and I couldn’t help but message. Any chance you’re free for a late lunch?

You know what? He wrote back. A couple hours later I was sitting across a bowl of udon noodles hearing all about his field work with birds and kinda liking him a whole lot. He walked me to my car and kissed me a bunch, which has been followed by  a slew of dates and last night’s Korean BBQ and I’m so very glad that I sent that text — even if common sense, self-respect and The Rules all shrilly screamed not to.

Interestingly, other single mom friends have had very similar experiences. Janet has enjoyed a wide swath of New York men (“mostly inappropriate,” she confesses, gleefully) since her divorce from her long-time marriage. About a year ago she told me about one man she went out with, who was the one who was not only the most appropriate, but the one she adored the very most. He stopped texting, which was not breaking any rules since their encounters were few, but she was still very disappointed.

Then, a few months ago, her amour still on her mind, she found herself near a restaurant where they had enjoyed one of their dates. She texted:

Hey Paul. I’m sitting near Tertulia and thought of you. Hope you’re well. 

Great news here, too. Turns out Paul had recently become untangled from the love interest who had snagged his attention away from Janet, was happy to hear from her, and now my friend has a fabulous new boyfriend.

The takeaway is that at this stage of life, dating is especially messy. Not only are there hardly any courtship rules any more, but if you’re divorced, a parent, or older than 28, you’ve almost guaranteed to have had your heart broken one or 12 times. You have responsibilities and ideas about relationships and a full life and history that makes the road to love nuanced, layered, complicated and confusing. If you’re going to get anywhere in this shit show, it requires a whole lot of forgiveness — forgiving yourself for feeling needy and vulnerable. Forgiving him for hurting you, or being inconsiderate or missing your cues. Forgiving and accepting that there are few rules to play by, and accept that you must be extra-kind, and sometimes extra-bold, in order to have fun and find love.

And sometimes, you need faith. Faith that a well-timed, if discouraged-by-your-friends, text can open doors to something special.

Just ask my old friend Lynne. A year after her divorce this single mom started a lusty long-distance affair with a beautiful, divorced European engineer — who unceremoniously dumped her six months in. She licked her wounds, dated a bit, but was compelled some months later to send him a text with a link to a funny news article related to an inside joke, with the note:

I thought you’d get a kick out of this. 

He did. They kept chatting, and are now a couple. This summer she’s traveling with him to Europe to visit his family. In dissecting the situation she said she held no grudges about his dumping her for an old flame who’d reached out. “There’s not a lot of room for sanctimony in post-divorce dating,” Lynn says. “Who the hell really knows what they’re doing? Mistakes — if you can even call them that — will and should be made.”

Anna’s thoughts dating ecologists:

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What do you think? Have you successfully reached out after getting dumped? Are there any rules in post-divorce dating? Share in the comments!


Emma Johnson is a veteran money writer, noted blogger, bestselling author and an host of the award-winning podcast, Like a Mother with Emma Johnson. A former Associated Press Financial Wire reporter and MSN Money columnist, Emma has written for the New York Times, Wall Street Journal, Forbes, Glamour, Oprah.com, REAL SIMPLE, Parenting, USA Today and others.

The Kickass Single Mom: Be Financially Independent, Discover Your Sexiest Self, and Raise Fabulous, Happy Children (Penguin, 2017), was a #1 bestseller and was featured in hundreds of media, including The New York Times, Wall Street Journal, Fox & Friends, Oprah.com and the New York Post, which named it to its ‘Must Read” list.

Her popular blog Wealthysinglemommy.com, and podcast Like a Mother, explore issues facing professional single moms: business and career, money, sex, relationships and parenting. Emma regularly comments on these topics for outlets such as CNN, Headline News, New York Times, Wall Street Journal, Fox & Friends, CNBC, NPR, TIME, MONEY, O, The Oprah Magazine, Woman’s Day, The Doctors, and many more. She was named Parents magazine’s “Best of the Web,” one of “20 Personal Finance Influencers to Follow on Twitter” by AOL DailyFinance, “Top 15 Personal Finance Podcasts” by U.S. News, and “Most Eligible New Yorkers” by New York Observer.

A popular speaker on gender equality, Emma presented at the United Nations Summit for Gender Equality.

Emma grew up in Sycamore, Ill., and lives in New York City with her children.

6 thoughts on “Why sometimes you should text him even when you think you shouldn’t

  1. Thanks for sharing this! I sent a text last weekend to a guy I had talked to about 6 months ago. My thoughts had gone back to him several times over the months. We had a nice chat but nothing came from it. But I’m glad I did because now I know for sure there is
    nothing there. I don’t feel awkward about doing it and we ended on a good note. I think about “the rules” but I usually go with my gut when it comes to these things!

    1. I find it refreshing at this stage of life that most people are really mature about dating. We all recognize that life can be very lonely. Love and life are complicated, timing is everything, and nothing is perfect. I’ll bet he was flattered you reached out, and it sounds like he was kind in his gentle rejection. Well played :)

  2. I one hundred percent agree. I’ve been dropped before and then re-connected months later. Once it’s done to you and your open minded and understanding then it opens doors. We all carry around a lot of stuff and we don’t necessarily share it with our dating partners. After reconnecting when you are dropped or you do the dropping then hopefully communication can clear up all the questions.

  3. I came across your blog yesterday and it was exactly what i’ve been looking. i am a single mum with the best son, will be 28 this july and am from Nigeria. i have always wanted to be myself and restore my glow by putting pen and paper together but i never knew how. Yesterday i read your blog on HOW I BECOME A WORK AT HOME WRITER AND BLOGGER AND HOW YOU CAN, TOO and you cant believe what happened. i’ve started writing something about me. All thanks to you.

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