by Lisa A. Beach
“I never imagined I would find myself in this situation,” you may reflect as you navigate the challenges of single parenthood after your divorce. Suddenly, you’re stepping into the uncharted waters of dating in midlife. It feels odd and awkward—nothing like the dating experiences of your youth.
Back in those days, dating was quite different. You didn’t have the influence of social media, smartphones, dating apps, or reality TV shows like The Bachelorette. At that time, you were younger, likely in better shape, without children, and just embarking on your career journey.
Now, you might be heavily involved in parenting or on the verge of becoming an empty nester. You are wrestling with social media, often seeking guidance from your teenagers to figure out how to upload photos or grasp the use of hashtags. You’re contemplating which online dating platform might suit you best as a more mature individual (Tinder? Match.com? eharmony?). Additionally, you’re attempting to take selfies that cleverly hide your wrinkles, bald spots, or love handles.
What’s a middle-aged single parent to do?
I consulted my friend Patty*, a single mother in her 50s, for her perspective. Divorced since 2005, Patty found herself single, raising two teenagers, and unexpectedly starting a new chapter in her 40s. Importantly, she recognized she wasn’t quite ready to dive into dating at first.
“Don’t start dating until you’re truly ready,” Patty advises. “You must ensure your heart is open and healed. It’s normal to feel hurt and disappointed, but harboring anger about the divorce will negatively affect your dating encounters.” She emphasizes the importance of being content with yourself before seeking companionship, noting that she felt ready to date when she encountered her ex and realized she had moved on emotionally.
Marcus*, a single father in his 40s, shares similar sentiments. “I’ve gone on so many dates where the women seem to carry more baggage than the DFW airport,” he comments.
Both men and women can bring emotional baggage to the dating scene. Past betrayals or negative experiences with ex-partners often lead to trust issues. Their hurt translates into a lack of faith in new relationships, leaving dates feeling the need to shout, “I am not your ex!”
When Patty eventually ventured into dating, she quickly discerned a pattern typical of first dates. “You have to address the elephant in the room,” she explains. Introductory dates often delve into how each person arrived at this point in their lives (divorced or widowed), whether they have children (and their ages), and specifics about custody arrangements. Although these conversations cover a lot of ground, they lay an honest groundwork for a potential second date.
With respect to parenting, being a single parent has likely fostered a sense of self-sufficiency, which can be empowering. While some might be put off by your newfound independence, others may appreciate that quality. If you’re on the brink of being an empty nester, you might want to steer clear of dating someone who still has younger children. Seek a partner who aligns with your current lifestyle—you’ve raised your children, and now you may desire someone to explore life with now that you’ve entered a new phase, or perhaps you yearn for a quieter life after a bustling marriage.
Throughout the years, Marcus has experimented with various online dating platforms, leading to both rewarding friendships and some “red flag moments.” He recounts experiences like being ghosted after weeks of dating and another date with someone who drank excessively and rambled about aliens and her past encounters with the law.
Patty has also explored online dating but has been on her share of blind dates, including one with a professor who used overly complicated language and suggested they meet at Denny’s for breakfast. “I realized that intellectual types aren’t my preference,” Patty remarks. “And Denny’s? Seriously?” (A suggestion: Always meet in a public space, but choose a location that enhances the romantic atmosphere. Fast-food chains and cheap breakfast spots don’t exactly scream romance.)
Ultimately, both Patty and Marcus are content with their solo lives but still hold out hope for finding that special someone. They are open to building a relationship but are equally okay if that never happens.
As for first-date advice, consider these straightforward suggestions:
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For safety, meet in a public place like a café or restaurant. Avoid letting your date drive you home; it’s prudent to keep your address private until you feel secure with them.
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For your peace of mind, plan an exit strategy. If you sense that the date isn’t going well, you’re not obligated to endure uncomfortable situations for hours. Arrange for a friend to call you at a predetermined time (like one hour in). If the date is enjoyable, ignore the call. If not, you can take the call privately and excuse yourself, offering a polite apology for needing to leave.
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Designate a special “first-date” outfit that you consistently wear for initial encounters. This helps prevent any wardrobe mix-ups with different dates.
- Who should cover the bill—man or woman? There is no definitive answer. A gentleman may rightly want to pay, but if you’re an independent woman who prefers to share the costs, feel free to do so.
*names changed for privacy
Dating Tips for Midlife Single Parents
Stay safe!
Utilize Google Voice for your phone number; it’s a free option. Refrain from sharing your home or cell number until you’re confident in the person you’re dating.
Do your homework by researching potential dates online. Examine their social media profiles and check platforms like LinkedIn to ensure they are who they claim to be. If needed, look into public records.
Selfies say a lot
Marcus provided this humorous yet poignant take on selfies in online dating profiles:
Tip #1: I can’t upload selfies until I shed 15 pounds!
Tip #2: I’ll take selfies, but only from the neck up.
Tip #3: Never date someone who only posts neck-up selfies.
Profile pictures reveal much about a person. For example, photos in front of a bathroom mirror can show what’s (or who’s) in the background. Does it appear clean? Is there clutter, like an ashtray or pets?
Create a checklist
Identifying your needs and non-negotiables will aid in assessing potential dates. Outline your ideal characteristics (sense of humor, kindness, humility, reliability) and any deal-breakers (intolerance, lack of job, rudeness). Patty, for example, dismisses any man who posts a shirtless workout photo, considering it a sign of someone trying too hard. A collective deal-breaker, whether male or female? “I’m a package deal,” responds Marcus. “If this develops into something, my date must accept that being a dad is my top priority.”
