Photo credit: OWN
OWN is bringing back its digital dating series Dating Download for a second season, giving viewers another look at the surprises, challenges and unexpected connections that can come with modern dating. Hosted by media personality Kendra G, the series returns Wednesday, November 18, with 10 new episodes.
The new season will premiere at 5 p.m. ET on OWN’s YouTube channel and social platforms. New episodes will arrive every Wednesday at the same time.
Known as “Kupid with a K,” Kendra G returns as the show’s host and matchmaker. She will guide singles through a dating experience designed to test whether their ideal partner on paper can also create a genuine romantic connection.
Kendra G returns as ‘Kupid with a K’
The central idea behind Dating Download is simple. Singles meet people who fit the qualities they say they want in a partner. Those qualities may include financial stability, ambition, entrepreneurship or attentiveness.
However, having the right qualities does not always guarantee chemistry.
Throughout each episode, participants navigate conversations, first impressions and unexpected moments. The dates challenge them to consider whether their expectations align with the person sitting across from them.
At the end of each date, guests must make one final decision. They can choose to “Download” and explore the connection further or “Delete” and move on.
That choice gives the series its signature format while highlighting a familiar dating dilemma. Sometimes, the person someone thinks they want is not necessarily the person with whom they connect.
Season 2 promises higher stakes, additional surprises and more candid reactions as the participants search for meaningful relationships.
Season 2 features 10 new dating stories
The upcoming season includes 10 episodes, each built around a different dating situation. The episode titles suggest a mix of humor, romantic expectations and questions about compatibility.
The lineup includes:
- EP201: The Shallow Queen Returns! Will She Find Her Prince?
- EP202: A Retired Hot Girl Seeking A Husband
- EP203: Can He Match Her Energy AND Her Lyrics?
- EP204: Looking For A Sanctified Baddie
- EP205: He’s Been Uncle Devin Long Enough!
- EP206: Can A Lover Girl Finally Get The Love She Gives?
- EP207: I Ain’t Got The Money, But I Got The Funny!
- EP208: 50, Fabulous and Done Wasting Time
- EP209: Is He Looking For A Wife or A Facebook Post?
- EP210: Is A Love Connection Worth Spinning The Block
The titles point to a range of dating priorities. Some participants appear focused on marriage and long-term commitment. Others are navigating attraction, financial expectations, personality and emotional compatibility.
The season also explores dating at different stages of life. One episode follows a 50-year-old woman who is ready to stop wasting time. Another centers on a woman who wants the same level of affection she gives to others.
Kendra G brings her matchmaking experience back
Kendra G leads the conversations with her dating knowledge and direct approach. As host, she helps participants examine their expectations and decide whether a potential connection deserves another chance.
Her role goes beyond introducing singles. She offers perspective on online dating, personal preferences and the difference between finding someone who checks every box and building a real connection.
The series uses those conversations to explore how people approach relationships in the digital age. It also invites viewers to consider whether their own dating standards help them find compatible partners.
How to watch ‘Dating Download’ Season 2
Dating Download Season 2 premieres Wednesday, November 18, 2026, at 5 p.m. ET. Viewers can stream the series exclusively through OWN’s YouTube channel and social platforms.
The 10-episode season will release one new episode every Wednesday at 5 p.m. ET.
Content.23 and Pauline Malcolm-Thornton’s BrandStory Architech produce the series.
With Kendra G returning as “Kupid with a K,” the new season puts another group of singles in the spotlight. Their choices will reveal whether the partner they imagined is the connection they actually want.
Source: OWN media alert
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