Advice & Features Articles

The Joys (and Pitfalls) of Dating as a Single Parent

by Lisa A. Beach

“I never thought I’d end up here,” you might be thinking as you ponder life as a single parent following your divorce. Now, you find yourself maneuvering through the unfamiliar territory of dating in midlife. It’s a bit strange and uncomfortable—not at all like dating in your teens and twenties. 

Back then, dating was a bit…different. You didn’t have social media, smart phones, dating apps, selfies or reality dating peep-shows like The Bachelorette. Plus, you were young, in better shape, childless and just starting out in your career.

Now, you’re either in the thick of active parenting or on the tail end of it ready to be an empty-nester. You’re navigating social media with the help of your teens, struggling to upload photos and understand hashtags. You’re figuring out which online dating site works best for more seasoned folks (Tinder? Match.com? eharmony?). And you’re trying to take selfies that minimize your wrinkles, bald spot or love handles.

What’s a middle-aged single parent to do?

I asked my friend Patty*, a single mom in her 50s, to share some insights. Divorced since 2005, Patty found herself single, raising two teenagers, and unexpectedly starting anew in her 40s. Wisely, she realized she wasn’t quite ready to date for a while.

“Don’t date until you know you’re ready,” Patty explains. “Your heart must be open and healed. While it’s okay to feel hurt and disappointed, you can’t still be angry about the divorce.” If you are, she says, it will color your dating experience in a negative way. Plus, you sometimes feel desperate when you’re freshly divorced, thinking anyone is better than no one. “You’ve got to be okay being by yourself,” notes Patty, who knew she was finally ready to date when she saw her ex and realized she no longer cared.

Marcus*, a single dad in his 40s, agrees. “I’ve been on so many dates with women who carry more baggage than the DFW airport,” he says. 

In fact, both men and women often carry baggage into their dates. Their exes cheated on them, so now they don’t trust any man or woman. Or they’re exes treated them badly, so now they have an attitude that all men or women treat their dates badly. This leaves their dates wanting to scream, “I am not your ex!”

When Patty finally did start dating, she quickly found a rhythm of how most first dates go. “You talk about the elephant in the room,” she explains. Those get-to-know-you-better first dates often focus on how you got where you are right now (divorced, widowed), whether you’ve got kids (how many, what ages) and, if so, where the kids live (with you, shared custody with the ex, away at college). It’s a lot of ground to cover on a first date. But it sets an honest foundation for a second date if that’s on the horizon.

Back to the parenthood issue. Being a single parent, you likely have become more self-sufficient, which is very empowering.  While some men (or women) can be turned off by one’s newfound independence, someone else could be the perfect match.  And, if you are soon to be an empty nester, you may not be inclined to date someone who is still in the midst of navigating life with tweens and teens.  Be on the lookout for someone who is a match to your personality now.  You’ve already raised your kids, and you may be looking for someone to see the world with now that your kids are young adults, or you may have been in a marriage that was go-go-go and prefer a match that enjoys quiet evenings at home.

Over the years, Marcus has tried a few online dating sites, which led to some wonderful friendships as well as his share of “red flag moments.” There’s the woman who ghosted him after several weeks of dating and the one who drank five shots of tequila and “talked non-stop about aliens, crazy exes and jail time.” 

Patty, too, has tried online dating, but she’s also been on her fair share of blind dates, such as the set-up with a professor who used scholarly, high-brow words and wanted to meet at Denny’s for breakfast. “I realized that intellectuals are not my type,” notes Patty. “And Denny’s? Really?” (Tip: Meet in public, but up your game when choosing the location. Fast-food burger joints and grand-slam-breakfast deals don’t exactly set the stage for romance.)

In the end, both Patty and Marcus are totally comfortable with their solo lives but would love to still find that special someone. They hold hope that they’ll meet the right person one day. But they’re also totally fine if they don’t. 

As for first-date advice, here are a few simple tips to follow:

1| For safety reasons, meet somewhere public, like a coffee house or restaurant. For the same reason, don’t let your date drive you home. You don’t want him or her to know where you live.

2| For sanity reasons, make an escape plan. If you sense the date is a huge dud, no need to stick it out for three or four hours. Ask a friend to call you at a pre-determined point in the date (say, one hour). If the date is going well, you simply ignore the phone call. If it’s not going well, you can take the call and excuse yourself to talk privately. Come back to your date, apologize and say, you’re sorry, but you need to leave. (It’s up to you if you’re comfortable telling a little white lie to avoid hurting your date’s feelings.)

3| Have a designated “first-date” outfit that you wear on every first date. That way, if you’re dating different people, you won’t forget and wear it again on date #2.

4| Who pays for the first date—man or woman? There’s no right answer. If you’re a gentleman, it’s always nice to grab the check. But if you’re an independent woman who doesn’t want to feel obligated once a man pays, feel free to cover your share.

*names changed for privacy

Dating Tips for Midlife Single Parents

Stay safe!

Use Google Voice, which is free, for your phone number. Don’t give out your home/cell phone number until you’re very comfortable and know this person well.

Do your due diligence by checking out potential dates online. Look into their social media accounts and check LinkedIn to see if they are who they say you are. If you feel the need, check for criminal records. 

Selfies say a lot

Marcus shared this funny-but-real insight on posting selfies on online dating profiles:

Tip #1: OMG, I can’t post selfies until I lose 15 lbs.! 

Tip #2: Okay, I’ll post selfies, but just from the neck up.

Tip #3: Never go out with someone with just a neck-up selfie.

But profile pictures do tell a lot about a person. Pics taken in front of a bathroom mirror, for instance, let you see what (or whom!) is in the background. Is he or she a clean person?  Is there an ashtray on the counter? Are there dogs in the background? 

Create a checklist

Know what you want and what you don’t want to help you evaluate potential dates. List your ideal characteristics (great sense of humor, strong faith, compassionate, good manners, humble, trustworthy, responsible) and any deal-breakers (prejudice, allergic to animals, smoker, rude, no job, self-absorbed). Patty nixes anyone with a shirtless photo of himself working out. (“Trying too hard to impress,” she explains.) A unanimous deal-breaker, whether you’re a man or a woman? “I’m a package deal,” explains Marcus. “If this relationship is going anywhere, my date needs to get that I’m a dad first and foremost.” 

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