“Send Me $110”: Post-Date Money Request Shocks Divorced Father, Seeks Advice Online
Dating again isn’t always easy—especially if you’ve been in a serious relationship for 10 years or more. Unlike riding a bike, getting back into the dating world can feel overwhelming. Today’s dating scene is completely different. Most people use online dating apps, and the old pick-up lines that once worked might now seem outdated or even awkward.
It’s very common to feel nervous or unsure when going on your first date after years. People have questions like: Who should pay? What should I say? How do I know if they’re really interested?
That’s exactly what happened to one man who shared his story on Reddit. After going on a date, the woman asked him to pay for the babysitter she hired for the night. This led to a big discussion online about dating etiquette, relationship boundaries, and what’s fair when dating a single parent.
We’ve included the full story below, along with expert insight from Cheryl Besner, a well-known relationship and communication coach. She shares professional advice on how to handle tricky dating situations, set clear expectations, and build healthy relationships from the start.
Whether you’re looking for dating tips for over 40, first date advice, or want to learn more about modern dating rules, this story can help you better understand today’s dating world.
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This man wasn’t sure what would happen on his first date post-divorce
But he certainly wasn’t expecting the woman to ask him to pay for her babysitter
Dating as a single parent comes with unique challenges
Most of us dream of falling in love. Even if you don’t want to start a family, having someone special to cuddle with at night sounds comforting. But these days, finding your perfect match isn’t always easy—especially if you’re a single parent or have been through a divorce.
According to the Pew Research Center, in 2020, about 75% of Americans said dating was hard. Nearly half believed dating has become even more difficult over the past 10 years. With the rise of online dating apps, changing values, and busy lifestyles, building a real connection takes more effort than ever before.
For single moms and single dads, dating can feel even more complicated. You love your kids and always put them first, but that doesn’t mean you have to give up on love. Still, many parents feel discouraged. A survey by the dating app Even revealed that 63% of single parents think they’ll never find love again.
To better understand this issue, we spoke with Relationship and Communication Expert Cheryl Besner. She explained why dating as a single parent is so different today.
“The number one challenge for any single parent is prioritizing and scheduling,” Cheryl shared. “When people re-enter the dating world, they usually say, ‘My kids are my priority.’ Many don’t even want their kids to know they’re dating, which makes planning even harder.”
Cheryl added that most single parents have to balance work, home responsibilities, and sometimes even caring for elderly parents. It takes real effort to make time for a romantic relationship.
“When two parents raise a child together, they can share responsibilities,” she said. “They might find couple time after the kids go to sleep. But single parents don’t always have that luxury.”
Another key challenge is how children react when their mom or dad starts dating again. Parents often think about their kids’ emotions before starting a new relationship.
“Not only is the person thinking about themselves in regards to future relationships, they’re also thinking about their children”
When it comes to dating as a single parent, money, time, and childcare can become real challenges. One question that often comes up is: Is it okay to ask your date to pay for your babysitter?
Relationship expert Cheryl Besner says that in most cases, the answer is no. Asking someone to pay for your babysitter on a first or early date might feel like too much too soon. But there are smart ways to make dating more manageable and affordable as a parent.
“Single parents can create a babysitting network with other single parents,” Cheryl suggests. “In many cities, there are even support groups that help with babysitting for dates, appointments, or emergencies.”
She also recommends asking family members for help or starting a co-babysitting group in your apartment building. These solutions can make it easier to enjoy your social life without putting pressure on a new romantic partner.
However, Cheryl says there is one exception:
“If the relationship becomes serious and frequent dates start adding up in cost, then it might be time to have an honest conversation about sharing expenses like babysitting.”
She also emphasizes the importance of self-care.
“Every single parent should have time for themselves—at least two hours a week. I call it ‘dating yourself.’ When you do this, it creates space in your life for when you’re ready to date someone else.”
Another key topic Cheryl talks about is introducing children to a new partner. Many single parents rush this step due to time limits, but it’s not always the best idea.
“Some parents end up introducing their kids to too many new people too quickly. That can create confusion and emotional instability for the child,” she explains.
As a divorced parent herself, Cheryl strongly believes you should wait until you’re sure the relationship is serious before introducing your children.
“Your children are watching you and learning how adult relationships work. So, think carefully about the message you’re sending with your dating choices.”
She also highlights a big difference in dating intentions:
- Are you dating for fun?
- Or are you looking for a serious, long-term relationship?
If it’s just for fun, Cheryl advises not involving your kids at all, to protect their emotional health.
Dating as a parent is never easy, but it is possible with the right support, boundaries, and mindset. Whether you’re looking for relationship advice for single moms, how to date after divorce, or childcare tips for single dads, it’s all about planning ahead and putting your children’s well-being first.
Readers assured the father that his date’s request was not normal, and many encouraged him not to see her again
