Dating as a Single Parent: Insights from Perfect Match's Jessica and Harry

Hi, my name is Lauren and I’m a reality television junkie. And if you’re here, reading this blog post, there’s a good chance you are too. So, welcome! I love a good reality television show — Real Housewives, The Challenge, Love Is Blind. I can’t get enough of the staged but chaotic situations, hilarious confessionals, and often outrageous personalities. And when the producers recycle the castmates, like MTV and Netflix tend to do, the chaos, hilarity, and outrage abound. This leads me to this past season (season 2) of Perfect Match.

I’m not in the habit of sharing my thoughts on every reality television show on this blog. (I use Twitter for that!) But I noticed as I watched this past season, that one of the matches on this past season of Perfect Match triggered me. And that’s worth discussing.

Meet Harry Jowsey and Jessica Vestal. Harry is your classic, blonde-hair-blue-eye playboy with a long and public history of using and discarding women. He’s appeared on Too Hot to Handle, Dancing With the Stars, Heartbreak Island, and Perfect Match. As Perfect Match progresses, we learn that he has left a string of disgruntled women at each reality television appearance. Jessica is a tiny but fiery, gorgeous, and cultured woman with a daughter and a complicated upbringing. She’s appeared only on Love is Blind where she was not chosen by her number one choice and delivered the classic comeback, “When you see and realize what you missed out on, you are going to choke. You are going to need your EpiPen to open up your airways because you are going to be in disbelief of what you missed out on” when he informed her of his choice.

After watching both Harry and Jessica in their respective shows, I didn’t even consider they’d end up together. And yet…

The Scenario

Harry and Jessica first met in Episode 2. Harry was matched with Elyse (who I love! But we’ll save that for another time) and Jessica was sent in as a new single and temptress. Their first date was cute. It was clear there was physical/sexual chemistry. And Harry responded thoughtfully to Jessica having a child, expressing admiration, respect, and a desire for family. And it is this moment that set the stage for Jessica hanging on and the many, deeper conversations they’d have throughout their relationship on the show.

Jessica often brought up her daughter's needs and the importance of finding a suitable partner for her and her child. Especially when Harry would do or say something questionable. And by questionable, I mean red-flag behavior. She’d respond to this behavior by reminding him of what she’s looking for in a partner and stepfather, hoping it would get him in line. This constant focus on her daughter placed considerable pressure on Harry, created tension between them, and highlighted the difficulties of balancing romantic interests with parental responsibilities.

Ultimately, they broke up. Harry was being Harry. Jessica got tired of dealing with it. And they unmatched.

The Struggle

When you're a woman dating with a child, there is an inherent pressure for the man you’re dating to be stepfather material. However, the pressure isn't on the man to grow or morph into this role. The pressure is on the woman to discern if he is already suitable stepfather material. This looks like having a beautiful mixture of empathy, patience, respect, open communication, consistency, reliability, and support. If he doesn’t have these qualities, he isn’t suitable stepfather material. Period. And the moment a woman discerns the man she’s dating isn’t stepfather material, it’s on her to stop the relationship from progressing. That is the pressure.

Jessica's struggle was she kept trying to get Harry to use her daughter as motivation for being a better man, and hoping it would teach him to be stepfather material. That’s too much! Too much work, too much pressure, too much expectation. We’ve already got a child to raise, we don’t need to raise a man, too.

Their dynamic highlights the challenges single women face in dating. Jessica's approach of frequently bringing up her daughter was her way of testing Harry's suitability but ended up backfiring by creating excessive pressure and wasting her time/energy. While Harry's manipulative tactics to win Jessica's favor by feigning concern for her daughter undermined trust and sincerity. Their relationship underscored the very delicate balance single parents have to strike between integrating new partners into the family and protecting their children from unsuitable influences. This situation shows the importance of self-awareness, discernment, and authenticity in relationships involving children.

Some Do’s and Don’ts of Dating with a Child

• Do’s:

  • Communicate Openly and Honestly: Be clear about your situation and your child's needs from the beginning. This helps in setting realistic expectations.

  • Prioritize Your Child's Wellbeing: Ensure that any potential partner understands and respects your child's needs and boundaries.

  • Take Your Time: Allow relationships to develop naturally without rushing to integrate your new partner into your child's life.

  • Observe Actions Over Words: Pay attention to how a potential partner interacts with children and handles responsibilities.

  • Seek Compatibility: Look for someone who shares your values, especially regarding family and parenting.

• Don’ts:

  • Avoid Immediate Introductions: Don’t introduce your child to every date. Wait until you’re sure about the relationship’s potential.

  • Don’t Force the Role of a Stepparent: Identify your partner’s stepfather material early, but avoid pushing them into the role before they’re ready.

  • Don’t Ignore Red Flags: Pay attention to any behaviors that suggest a lack of commitment or respect for you or your family.

  • Don’t Make Comparisons: Avoid comparing your new partner to your child’s other parent, as it can create unnecessary pressure.

  • Don’t Overlook Your Needs: Remember to balance your needs with those of your child to maintain a healthy relationship for everyone involved.

The Takeaways

Dating as a single mom presents unique challenges, as we can see with Jessica and Harry on Perfect Match. While it's important to find someone who can be a positive presence for both you and your child, it’s equally important to maintain clear boundaries and realistic expectations. Jessica’s experience highlights the importance of discerning a partner’s true intentions and suitability for your family life. By following these do's and don'ts, single moms can navigate dating more effectively, ensuring both their happiness and their child’s well-being.

If you're a single mom navigating the dating world, remember that your journey is unique and valuable. Prioritize your well-being and your child's needs, and seek relationships that respect and enhance your family dynamic. What are your thoughts on Harry and Jessica? Share them in the comments!

For more insights and advice, subscribe to my blog and stay tuned for upcoming posts on how I navigated dating as a single mom.