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The Single-Mom Dating Guide

Date night

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Several months after my husband and I separated, it finally occurred to me that I was free to date. It was a concept both thrilling and terrifying. The last time I'd been single, I'd had copious amounts of free time, was beholden to no one, and believed in love. Now, however, I had 16 years of marriage and 11 years of motherhood under my belt, plus a less-than-starry-eyed attitude about romance. And did I mention the two precious, innocent little girls who needed me to be there for them?

Trying to simultaneously be a hot mama and an uber-responsible single parent was a challenge to my schedule and my psyche, but I learned that you can, in fact, have a romantic life without freaking out your kids (or yourself). I've been at it for three-plus years now, so let me take a stab at what I suspect are your most pressing questions--they were surely mine.

How Will I Know When I'm Ready to Start Dating?
I know people who waited years before deciding to take the plunge and some who threw themselves into it instantly. There's no right or wrong, but you should date only because you want to, not because anyone else thinks you should or shouldn't. Believe me, people will have opinions... lots and lots of opinions.

If there's another parent in the picture and you share custody, you will suddenly have something called free time, which you may remember from your pre-mom days. (If you're the solo caregiver, please put down this magazine and make yourself a roster of babysitters because you'll need a break.) I remember finding those first few weekends sans kids heady and horrible at the same time. One minute I was dancing around the living room singing "Do you believe in life after love?" with Cher and the next I was weeping because my daughters weren't there to cramp my style. Without playdates to supervise, squabbles to moderate, or mac 'n' cheese to make, it's hard to know who you are at first.

"I had to take a step back and process what had happened in my marriage," says Jennifer Fink, a mom of four from Mayville, Wisconsin. "I went to a therapist, wrote in my journal, and spent time with my friends and family. I was afraid that if I jumped right back in, I'd just end up in another unhealthy relationship with someone else--which wouldn't be good for me or my kids."

She took the plunge about five months after she and her husband separated. I decided to enter the fray about four months after my ex-husband moved out. How did I know it was time? For one thing, I couldn't bear to face another kid-free weekend doing jigsaw puzzles or watching English period dramas. And I found myself lusting after a headless male mannequin in the Gap.

I'm Ready to Date, But Where the Heck Do I Begin?

Wait--so you're saying there isn't a line of handsome, well-adjusted suitors waiting outside your door because they got the memo that you're available? There were no obvious candidates for me right off the bat either. Also, I found much of the common wisdom, which advises the single gal to ask friends to fix her up or to hunt for hunks in the aisles of The Home Depot, maddening and unrealistic.

By all means, get the word out that you're interested in meeting someone and cross your fingers. People do get fixed up, from what I hear, and I suppose there are women who can make things happen at bars, playgrounds, and big-box chain stores. I'm not one of them.

The fact is, you're a busy mom, which means you're often housebound. If you want to have some control over the process, carve out a few hours for yourself and your laptop during your kids' naptime or after they're asleep. Sniff around on Facebook. (Surely there's an old flame, or a friend of a friend of a friend worth, um, friending?) Or join an online dating site where you can cast your net as wide as you'd like. Your married friends will eagerly help you write your profile and, in return, you will provide them much-needed vicarious thrills. They will love it, I promise!

Should I Date Only Dads?

Maybe. Having children is such a life-altering experience that it can be hard to relate to men who don't get the intense pull on your heart and pressure on your time that is parenthood. In my three-plus years of postmarital singledom, I've gone on one or two dates with non-dads, but my two longer-term relationships have been with fathers. Men who haven't been in the parenting trenches, even if they love kids, just seem to speak a different language, one that doesn't necessarily have a translation for phrases such as, "I can't leave my son with a babysitter tonight because he has the flu."

On the other hand, dating a man with kids can be a scheduling nightmare, requiring both of you to synchronize with your exes and their new love interests, and the new love interests' exes, ad infinitum. Julia Landry, the author of the parents.com blog Unexpectedly Expecting, where she chronicles her life as the single mom of a 3-year-old, says she prefers to date dads: "They're less likely to unfairly judge me for being a single mom and they understand that my child will always come first." But Landry doesn't promote a hard-and-fast rule. "Non-dads tend to be able to work better with the crazy schedule of a single mom," she says. The bottom line: There's no explaining chemistry. If it works with someone, it works, dad-ness be damned.

When Is the Right Time and What Is the Right Way to Introduce a Guy I'm Dating to My Kids?

Can I tell you how much I dreaded this? Okay, I will. I was dating a guy for a couple of months when my girls, then 8 and 12, got wind of his existence. Because their dad had already introduced them to his girlfriend and everything went fine, I figured they wouldn't give me a hard time. But they're girls and I'm their mom, so it was a whole different thing. My older daughter was not cool with my even mentioning my boyfriend and announced that she refused to meet him. Ultimately, about eight months into it, I invited him to join us at a dinner party with some family friends. He and the girls got to interact casually in a group setting, without him feeling like he was on a job interview.

Still, there's no right or wrong way to do the meet-and-greet, and there are so many potential variables, including the age, sex, and personality of your kids. Infants and toddlers won't register that this is Mommy's new boyfriend. Older kids' reactions could run the gamut from very threatened to seemingly indifferent. My friend Kristin Cole, who lives in Montclair, New Jersey, recalls that her 10-year-old announced that he was going to say "I hate you! You're not my dad" upon meeting her boyfriend. What really happened is that they tossed a football around in the yard and ended up becoming pretty chummy. Much will also depend on how your beau handles himself.

A few rules of thumb for you: Tell the kids about your new guy after you've been dating him for a few months and believe the relationship is likely to continue. There's no reason to put everyone through the meet-up if he's going to be history next week. Maybe show them a picture of him or let them answer the phone and hear his voice to help de-mystify him. Feel them out, and keep a first meeting brief and casual, and expectations low. (For instance, don't say, "You are going to just adore Jeremy!") And definitely avoid any and all PDA.

Can My Boyfriend Sleep Over When My Kids Are Around?

Not so much. No matter if your kid is 3 or 13, she does not want to witness you sucking face with someone who's not her father. (That's gross, Mom!) As a single mom with a boyfriend, you need to lead something of a double life until a relationship gets serious. Have sleepovers with your guy, but do them on your own time, when your ex has your kids or they're at Grandma's.

Once you're really, solidly a couple, how you handle this depends a lot on your own values and the age of your kids, and how long you and your guy have been together. Fink feels strongly about keeping her sex life and her parenting life completely separate. Cole, who's a little more freewheeling, has her boyfriend stay over frequently, but they've been together for a few years. The one time my boyfriend stayed over, we both wore full-coverage flannel pj's--and kept them on all night.

What If My Kids Get to Know Someone And Then We Break Up? Won't They Be Traumatized All Over Again?

When you're out there dating, there's a good chance that you will end up breaking up with someone along the way. If your kids have become close to the man, they may be bummed but they won't be destroyed. (And they may even manage to stay in touch.) When my boyfriend of 18 months and I broke up, I dreaded telling my daughters.

I was frankly a little embarrassed that another relationship hadn't worked out and wondered what kind of role model I could ever be. I avoided saying anything for about two weeks. Then my older daughter asked me point-blank if we'd broken up. I said yes. "I knew it!" was her reply, followed by "Honestly, Mom, you can do better."

Despite its pitfalls, Landry thinks staying in the dating game is worth the risk for the chance for her child to see her in a happy and healthy relationship. "Just because her father and I didn't work out doesn't mean that both he and I can't serve as good relationship role models in the future."

Originally published in the October 2012 issue of Parents magazine.