Dating With Kids: 12 Tips for Single Moms

Dating with Kids: 12 Tips for Single Moms

Dating with kids can be challenging – whether you’re recently divorced or you’ve endured two years’ worth of Starbucks dates -- and whether your kids are two or twenty-two. But your children can be helpful as well, especially if you recognize their wisdom. Here are a dozen tips on how they can help or hinder your social life.

1) First things first. After 20 years of puttering around the house in your ex-husband’s tattered Sigma Epsilon sweatshirts, size XXXL, you’ll need to spruce up your wardrobe. Here’s where your teenage daughter can be an invaluable asset. Set her loose in your closet, armed with an industrial-size trash bag. Close your eyes and trust her as she dumps your frump-wear: baggy sweats, grubby T’s, maxi skirts, clodhopper shoes. In short, anything that makes you look like Granny from “The Beverly Hillbillies.”

2) However, this doesn’t give you license to start dressing like the Olsen twins and cause your children endless embarrassment. Stay out of the teen department, and avoid those eensy-weensy mini-skirts, baby-doll tops, and low-rise jeans that display your new red thong. Let your children play the hosts on your personal version of “What Not to Wear.” You’ll know you’ve gone way too far if your daughter says you look like a “skank,” and your son asks if you’re decked out for a dance at the middle school.

3) Now that you’ve made the leap from soccer-mom stodgy to single-mom sexy, you’re ready to meet some guys. Again, here’s an area where it can actually help to have children. Keep your eyes open for attractive single dads when you pick up your kids from track meets, driver’s ed, SAT prep, CCD class, or Bar Mitzvahs. But whatever you do, NEVER date the father of your child’s friend. Believe us: this will make the kids gag.

4) You spent your adult life living side by side with your ex-husband, 24/7. The upshot? You know nothing about men. At this point, your children’s creep radar is a thousand times keener than your own. So if you show a guy’s internet dating profile to your teenage daughter for pre-approval, and she points out that he’s a dead-ringer for the Unabomber, listen to her.

5) When was the last time you went out on a date anyway? It was a different century! It’s as if you were cryogenically frozen 20 years ago and just thawed out. You’ll find yourself grilling your teenagers about when to return a guy’s call, how to open a text message, what to write on your internet profile. With great condescension, they’ll deliver a painfully elementary lecture on the how-to’s of handling men. Take notes.

6) Eventually you’ll catch up and hone your own instincts about whom to date. And sometimes, you can use your kids as a barometer. For instance, if a guy invites you to a pricey, five-star dinner at Auberge d’Argent, and you’d rather stay home and watch “South Park” with them, trust that impulse.

7) Of course, your kids will only be helpful up to a point. The same 15-year-old who proofread your internet dating profile might feel possessive once you’re actually dating. She may need reassurance that she’s still the most important person in your life -- especially if she suddenly demands your help with algebra on Saturday nights.

8) Your teenagers may also feel protective when you start dating. Just as you need to know when they’ll be home, remember to show them the same courtesy. Otherwise, don’t be surprised if they call your cell at 1:30 a.m. while you’re out on a date, and offer, “If you’ve been drinking, we’ll pick you up wherever you are – no questions asked.”

9) Keep in mind that your children still picture you sitting home every night, just waiting for the chance to roast a chicken for them. So be prepared for your college freshman to pop home unexpectedly, laundry bags and roommates in tow. Don’t get caught making out with your new boyfriend in front of the kitchen window.

10) No matter how mature your daughter is, do not update her on your decision to sleep with the guy you’re seeing. Or for that matter, tell her anything about your sex life. Remember, she’s your child, not your friend. In her words: “Like, too much information. Gross.”

11) Dating with really young kids poses a special challenge. Babysitters are a budget-breaker, and besides, you might feel guilty going out on Saturday night rather than staying home and playing Candy Land. But if you’re organized and highly energetic, you can have it all. Just feed them, bathe them, read The Cat in the Hat, and tuck them in. Then bring out the candles and wine, and whip up a 30-minute meal for two at 8:30. It’s a lot of work, but a welcome break from those 5:30 dinners of Scooby-Doo mac ‘n’ cheese with dinosaur-shaped chicken nuggets. Yum.

12) The advantage of dating with little kids is that they’ll welcome your new boyfriend so long as he gives them a high-five and a bag of pretzels. Not so when they’re older and wiser. Don’t expect them to like any guy you date within the first year of your divorce, even if he offers them World Series tickets and a keg of beer. But by now your radar is working and you know the ropes, so if you think he’s worth it, hang in there. Your kids will come around. Maybe.