by Lisa A. Beach
“I never imagined I’d find myself here,” you might reflect as you navigate life as a single parent post-divorce. Now, you’re exploring the new landscape of midlife dating, which feels rather strange and awkward—certainly not like the dating experiences of your youth.
In younger years, dating was rather… different. You didn’t have social media, smartphones, dating applications, selfies, or reality dating shows like The Bachelorette. Additionally, you were younger, possibly in better shape, without children, and just embarking on your career journey.
Now, you’re either deeply engaged in the demands of active parenting or nearing the empty-nester phase. You’re learning to navigate social media with support from your teens, battling to upload photos and decipher hashtags. You’re investigating which dating site is more suitable for adults (Tinder? Match.com? eHarmony?). And you’re attempting selfies that downplay your wrinkles, balding, or love handles.
What is a middle-aged single parent supposed to do?
I turned to my friend Patty*, a single mom in her 50s, for some insight. After her divorce in 2005, Patty found herself single, raising two teenagers, and unexpectedly starting again in her 40s. Recognizing this transition, she wisely chose to take a break from dating for a time.
“Don’t date until you are genuinely ready,” Patty advises. “Your heart needs to be open and healed. While it’s natural to feel hurt and disappointed, you mustn’t still harbor anger about the divorce.” If unresolved anger persists, she warns, it can negatively affect your dating experiences. Freshly divorced individuals often feel urgency, believing that anyone is better than being alone. “You’ve got to be okay being on your own,” Patty emphasizes, recounting how she knew she was ready when seeing her ex without any lingering feelings.
Marcus*, a single dad in his 40s, concurs. “I’ve been on numerous dates with women carrying more baggage than the DFW airport,” he remarks.
Indeed, both men and women frequently bring emotional baggage into their dates. Previous infidelities cause mistrust in potential partners, or negative past relationships lead individuals to assume all others will behave similarly. This often leaves date partners wanting to shout, “I am not your ex!”
When Patty finally ventured back into dating, she quickly discerned the common dynamics of first dates. “You discuss the elephant in the room,” she shares. Initial conversations often touch on how each person arrived at this point (divorced, widowed), whether they have children (how many and their ages), and where the kids live (with them, sharing custody, or at college). It’s a lot of ground to cover on a first date, but it establishes a sincere foundation for a potential second date.
Regarding the parenting aspect, as a single parent, you’ve likely become more self-sufficient, which can be quite empowering. While some individuals may be deterred by this newfound independence, others might appreciate it as a perfect match. Also, if you are about to become an empty nester, you may not be interested in dating someone still navigating the challenges of raising teens. Seek out someone whose personality aligns with where you are now. You’ve raised your children and might want to connect with someone to explore life alongside now that your kids are young adults, or you may prefer a partner who enjoys quieter evenings if your past marriage was hectic.
Over the years, Marcus has explored several online dating platforms, resulting in both meaningful friendships and a few “red flag moments.” He recalls a woman who ghosted him after several weeks and another who consumed five shots of tequila while “talking non-stop about aliens, crazy exes, and jail time.”
Patty has also ventured into online dating but has experienced her fair share of blind dates, including a meetup with a professor who used pretentious language and suggested meeting at Denny’s for breakfast. “I realized that intellectuals are not for me,” Patty notes. “And Denny’s? Really?” (Tip: Choose a public place, but elevate the venue for romance. Fast food and diner breakfasts aren’t ideal.)
Ultimately, both Patty and Marcus are comfortable in their individual lives but hope to find that special someone. They remain optimistic about meeting the right partner someday while also being perfectly fine if that doesn’t happen.
Here are some first-date tips to consider:
1| Prioritize safety by choosing a public meeting place, such as a café or restaurant. Similarly, avoid having your date drive you home; keep your address private until you feel secure with them.
2| Prepare an escape plan for your own peace of mind. If a date turns out to be a disappointment, there’s no need to endure a lengthy experience. Arrange for a friend to call you at a pre-arranged time (perhaps after one hour). If the date is enjoyable, simply ignore the call. If it’s not going well, take the call and step away to speak privately. Upon returning, apologize and explain that you need to leave. (You can choose whether to tell a small lie to spare their feelings.)
3| Have a specific “first-date” outfit that you wear each time. This way, if you’re dating multiple people, you avoid the chance of wearing the same outfit for a second date.
4| Understand the expectations regarding who covers the cost for the first date. There is no definitive answer. A gentleman may prefer to pay, but if you’re an independent woman who dislikes feeling obligated, feel free to split the bill.
*names changed for privacy
Dating Strategies for Midlife Single Parents
Stay secured!
Utilize Google Voice, which is free, for your phone number. Avoid sharing your personal mobile number until you feel comfortable and develop trust with the other person.
Conduct background research on potential dates online. Explore their social media pages and check LinkedIn to verify their identity. If necessary, look for criminal records.
Selfies convey a lot
Marcus provides this humorous yet truthful perspective on uploading selfies for online dating profiles:
Tip #1: OMG, I can’t post selfies until I lose 15 lbs.!
Tip #2: Okay, I’ll post selfies, but only from the neck up.
Tip #3: Never agree to meet someone with just a neck-up selfie.
Profile pictures provide significant insight into a person. Pictures taken in front of a bathroom mirror allow viewers to assess cleanliness and the surroundings in the background. Is the individual tidy? Is there an ashtray on the counter? Are there pets visible?
Create a checklist
Know your wants and needs to assist in evaluating potential partners. Draft a list of your ideal traits (sense of humor, strong faith, kindness, good manners, humility, honesty, and reliability) and also identify deal-breakers (prejudice, animal allergies, smoking, rudeness, unemployment, or self-centeredness). Patty dismisses anyone who shares shirtless workout photos, stating, “Trying too hard to impress.” A common deal-breaker for both men and women? “I’m a package deal,” Marcus notes. “If this relationship is to progress, my date needs to recognize that I’m a dad above all else.”
