Who should make the first move when dating? McKenzie Stout believes women should feel comfortable making the first move, while Rachel Cuello believes men should take the lead. Then, David Egbo and Nick Suh join the conversation to share their perspectives and get real about what the dating scene looks like today.
Next, singles expert Kendra G joins the Tam Fam to talk about OWN’s new digital series, “Dating Download.” Raven Small and Gracie Abercrombie also join the conversation to share why they are choosing to stay single in today’s digital dating age. Plus, Kendra and Tamron have an honest conversation about dating expectations and whether setting the bar too high can make it harder to find a connection.
Would Kendra G ever date a significantly younger man and become the “sugar mama”? Apparently not!
When the idea was tossed out that she could date a 35-year-old man with no children who could show her a great time for the weekend as long as she covered both plane tickets Kendra immediately shut that down. Her response was essentially, Absolutely not! After all, she pointed out, she has nieces and nephews around that age, so she’s certainly not about to start buying plane tickets for a grown man.
Back on the show, Kendra G continued her conversation about the realities of modern dating and her new series, Dating Download.
The discussion turned to the traditional “dating chase” and an interesting observation from a younger group of singles. Despite being under 30, the panel had surprisingly traditional expectations when it came to relationships. They believed men should generally make the first move, plan the date and pick up the check.
Kendra explained that dating doesn’t follow one universal formula. Some women will naturally make the first move, while others will find themselves being approached. For her, however, getting approached has never really been the issue.
She jokingly explained that she has always attracted attention, but as her career and personal style evolved, so did the attention. She reminisced about her college days and admitted that upgrading her hair made a noticeable difference. Apparently, the wigs were doing some serious work!
But when it comes to dating “rules,” Kendra believes there’s one thing people should pay attention to: who is actually showing interest in you.
Her philosophy is straightforward. If someone genuinely likes you, you shouldn’t have to constantly pursue them or convince them to spend time with you. Interest should be apparent through their actions—they’ll make plans, initiate contact and find opportunities to see you.
The conversation then moved into Kendra’s work with women who appear on Dating Download. She explained that many of the women arrive with very specific expectations about their ideal partner, sometimes creating an almost fantasy-level checklist.
Height, appearance and other physical characteristics can become prerequisites before they’ll even consider someone.
Kendra believes those expectations can sometimes be less about having standards and more about protecting yourself from rejection.
She pointed out that if thousands of women are looking for the exact same combination of qualities, it is worth asking whether those characteristics are really the foundation of a healthy relationship—or simply what someone has decided they need to feel secure.
The discussion also touched on the complicated subject of physical attraction. Kendra acknowledged that appearances can be misleading because outsiders never know what actually happens inside someone’s relationship.
Someone might not fit another person’s idea of the “perfect” couple based solely on looks, but that doesn’t mean they don’t have a meaningful connection.
She also pushed back on the idea that encouraging someone to broaden their dating preferences automatically means telling them to “settle.” For some women, hearing that they should reconsider a particular requirement can feel like being told they aren’t worthy of the person they originally envisioned.
That, Kendra explained, is where the conversation becomes complicated.
Tamron agreed that dating expectations can sometimes be tied to deeper fears about rejection. People may create long lists of requirements as a way of protecting themselves emotionally, rather than giving themselves the opportunity to discover whether someone is actually compatible with them.
The conversation wasn’t simply about lowering standards—it was about understanding the difference between genuine compatibility and using an idealized checklist as emotional armor.
Kendra has now taken those conversations beyond one-on-one discussions and onto the screen with Dating Download. After completing the first season, she announced that a second season is on the way through OWN’s YouTube channel.
But perhaps the most meaningful moment came when Kendra turned the conversation toward Tamron.
She revealed that several years earlier, she made the difficult decision to leave her radio job after feeling that she wasn’t genuinely being considered for a promotion. At the time, she thought about Tamron’s own career journey and the decision she had made to walk away when she knew she deserved something more.
Kendra said Tamron’s example gave her the courage to make her own leap of faith.
She told Tamron that if she hadn’t taken that step, she wouldn’t be hosting Dating Download today.
The heartfelt admission earned a huge reaction from the audience, with Tamron clearly touched by Kendra’s words.
And just like that, what began as a conversation about dating turned into something much bigger: a reminder about recognizing your own value, taking a chance on yourself and being willing to walk away when something no longer feels aligned with where you’re headed.
Of course, Tamron couldn’t let the emotional moment go on for too long without joking that Kendra was simply trying to make her cry and distract everyone from the dating conversation!
And with that, the show teased another fascinating dating story ahead: a 60-year-old woman, a 40-year-old man, and the surprising details of who made the first move.
Tamron wearing a Johanna Ortiz Serene Safari Draped Ankle dress, pretty!
(Disney/Jeff Neira)
