“Send Me $110”: Post-Date Money Request Shocks Divorced Father, Seeks Advice Online

Dating isn’t exactly like riding a bike. If you’ve been in a committed relationship for the past decade, jumping back into the dating scene might be extremely daunting at first. Times are constantly changing, everyone seems to be on the apps these days, and the pick-up lines you used on your ex might not have the same ring to them anymore.

So it’s perfectly normal for anyone who’s going on their first date in years to have some questions about what’s to be expected. That’s why one man recently reached out to Reddit after his date asked him to pay for the babysitter she hired. Below, you’ll find the full story, as well as a conversation with Relationship and Communication Expert Cheryl Besner.

This man wasn’t sure what would happen on his first date post-divorce

A man and woman walking in a park, engaging in a conversation, with trees in the background.

Image credits: Katerina Holmes/Pexels (not the actual photo)

But he certainly wasn’t expecting the woman to ask him to pay for her babysitter

Man confused after date demands payment for babysitter, text on gray background.

Text message recounting a date with babysitter payment confusion.

Text conversation about a date at a Greek restaurant and bar; confusion over paying for a babysitter.

Text about a successful date, with a mention of walking her home and kissing goodbye.

Text exchange about date requesting money for babysitter, leaving guy confused about the situation.

Man looking confused while on a phone call, wrapped in a striped blanket, outdoors.

Image credits: RDNE Stock project/Pexels (not the actual photo)

Text excerpt discussing a date where a man feels paying for a babysitter is excessive.

Text about understanding that kids are part of pursuing a relationship, related to confusion over a babysitter demand.

Man puzzled by date asking him to pay babysitter, no prior agreement noted.

Text on a white background discussing dating concerns and asking for advice.

Text about a man's date asking him to pay for her babysitter, leaving him confused.

Image credits: throwRa7273628

Dating as a single parent comes with unique challenges

Image credits: Josh Willink/Pexels (not the actual photo)

The majority of us are interested in finding love. Even if you have no desire to start a family, the idea of finding “the one” and having someone to snuggle up next to every night in bed may sound like a dream. But finding your perfect match might not be easy, and it may be even harder for you than it was for your parents or older siblings.

The Pew Research Center reported in 2020 that three quarters of Americans were finding it very or somewhat difficult to find people to date in the past year. And nearly half said that dating has become more challenging for the majority of people over the past decade.

So it’s no surprise that finding love can be even more complicated for single parents. Moms and dads will always be committed to putting their little ones first, but that doesn’t mean that they should completely give up on romance after going through a breakup or divorce. 

Not everyone is positive about the future, though. A study conducted by the dating app Even found that a whopping 63% of single parents believe they’ve “never find love again.” And the reality is that dating as a parent can be tough.

To learn more about this, we got in touch with Relationship and Communication Expert Cheryl Besner. She was kind enough to have a chat with Bored Panda and discuss how dating is different for parents.

“The number one challenge for any single parent in all aspects of their life is prioritizing and scheduling,” the expert says. “In my line of work, usually the first comment out of a single person re-entering the dating world will be ‘My kids are my priority.’ For many, they don’t even want their children to know that they are starting to rebuild their social life, and that might be for many reasons, and that is where scheduling comes in to play.”

“As in most cases, the parent has to juggle between work, running the house and other responsibilities like, for example, aging parents,” Cheryl continued. “It has to then become a conscious effort to carve time into their life to date.”

“Remember, when two people are raising a family, they have somebody to hand off [responsibilities] to when they need personal time,” the expert noted. “And couple time is often spent at the end of a night when the children have gone to sleep. This does not exist anymore as they enter the dating world.”

Cheryl says another difference is parents have to consider how their kids will react to them dating. “In many cases, not only is the person thinking about themselves in regards to future relationships, they’re also thinking about their children.”

“Not only is the person thinking about themselves in regards to future relationships, they’re also thinking about their children”

Image credits: Tatiana Syrikova/Pexels (not the actual photo)

As for whether or not it would be appropriate for a parent to ask their date to pay for their babysitter, Cheryl says, in general, no. But there are ways parents can make dating more accessible.

“For example, single parents can build a network of babysitters amongst themselves,” she pointed out. “In some cities, there are even single parent groups that help each other, not just in the form of dating, but appointments in general.”

“If you live in an apartment building, start a co-babysitting group if one does not already exist, or ask family members for help,” the expert continued.

“The caveat would be if the relationship continues and there are too many invitations, and a person cannot always afford help,” Cheryl added. “Then I think at that point, it can be a discussion with the other individual.”

“Part of my belief is that every single parent should find time for themselves, even if it’s just for two hours a week,” she shared. “I called it ‘dating yourself’, an important part of self-care. If you set that up, you automatically have time to date when when the time comes.”

Cheryl pointed out that another important aspect of single parenting and dating is when to introduce the children. “Sometimes, because of scheduling conflicts, people rush into introducing the children too quickly because it is more convenient to spend free time with both their children and their newfound relationship person,” she says. “However, this can lead to too many introductions to too many ‘potential’ individuals.”

“As a divorced person myself, I strongly recommend taking the time to decide if this person is truly someone you see yourself developing a relationship with before making those introductions,” the expert continued. “I have met and interviewed many people who have had a revolving door of people meet their children. It’s important to remember divorce causes instability in a child’s life, and the last thing they need is to continuously have more people enter and exit their world.”

“A big distinction is understanding the difference of intention. For example, is somebody entering the dating world just to have fun and date? Or are they looking for a long term relationship? In the first case, no interaction would be the best policy for the well being of the children,” Cheryl told Bored Panda.

“It’s important to remember that we, as parents, are teaching our children how adults interact and build relationships. They learn from our example,” she shared. “So, no matter what we are doing, think about the lessons being taught when it comes to your dating life.”

We would love to hear your thoughts on this situation in the comments below, pandas. How would you have responded to this mother’s request to pay for her babysitter? Then, you can find another Bored Panda article discussing similar issues right here. 

Readers assured the father that his date’s request was not normal, and many encouraged him not to see her again

Comment discussing a date's babysitter request as incredibly tacky, with 7.2k points.

Comment on a social media post: "Asking for babysitting money on a first date is crazy.

Comment on a post about a guy confused by a date’s demand regarding a babysitter.

Reddit comment discussing confusion over paying for a date's babysitter, with advice against it.

Comment discusses confusion over date's babysitter demand.

Reddit comment reading "HUGE RED FLAG" about paying for a babysitter on a date.

Reddit comment on date refusing to pay for babysitter, calling it outrageous and ridiculous.

Reddit comment expressing confusion over date requesting babysitter payment.

Text post about a confused guy whose date demands he pay for her babysitter, calling it tacky.

Comment discusses a date's demand for babysitter payment, calling it inappropriate and advising against future dates.

User comment discussing date babysitter payment expectations.

Reddit comment mentions paying for a date's babysitter as "not normal," suggesting further demands.

User comment on paying for babysitter during a date, calling it a financial red flag.

Comment suggests babysitting date's kid to earn 100 euros, related to confusion over paying for babysitter.

Reddit comment about not paying for a babysitter on a date as it's not the guy's responsibility.

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