Tommy Miles on Love, Legacy & Keeping It Real: Inside Ready to Love’s 10th Season

When Tommy Miles — better known as “Nephew Tommy” — walks into a room, he doesn’t just host; he commands the vibe. For ten seasons, the smooth-talking matchmaker has been the heartbeat of OWN’s hit dating series Ready to Love, guiding singles in their 30s and 40s through the messy, magical journey of finding real connection. Now celebrating a staggering 150 episodes, Tommy reflects on why audiences keep showing up — and why, when it comes to Black love, authenticity still wins every time. Tommy can’t hide his excitement when we bring up the milestone.

“This is big. One hundred and fifty episodes — that’s nothing to take lightly,” he says with a grin. “Season one in Atlanta, I would’ve never thought we’d be here. This is a blessing.”

For Tommy, the secret sauce behind Ready to Love’s staying power is simple: realness. The show resonates because the cast reflects a familiar spectrum of modern love stories. “We’ve got people in their mid-30s, 40s, even late 40s,” he explains. “Folks who’ve been through heartbreak, career shifts, detours — people who’ve hit bumps and bruises but are still out here believing in love. That’s why viewers connect. They see themselves, their friends, their girlfriends, their cousins on that screen.” And Tommy’s right. Ready to Love doesn’t just showcase romance; it mirrors the audience back to themselves. “When you’re watching the show,” Tommy laughs, “you see someone and go, ‘Oh my God, that’s my girlfriend acting just like that,’ or, ‘I know a brother who trips exactly like that.’ It’s real — that’s us.”

Throughout the interview, Tommy drops wisdom that feels part uncle, part coach, part best friend. When we ask about singles trying to find love later in life, he doesn’t hesitate.

“The first thing? Patience,” he says firmly. “A lot of us find something, but that don’t mean we found it. You gotta unpack the bag, piece by piece. Everything shiny ain’t for you. Take your time, figure out what you can live with and what you can’t.”

In today’s swipe-right culture, Tommy stresses that slowing down and staying grounded is key — especially for people reentering the dating scene after years away. And one thing he thinks everyone could do better? Communicate.

“Let’s try talking face-to-face again,” he says. “We get lost in texting, lost on social media. Back in the day, we’d stay up all night on the phone, just talking. That was how you got to really know somebody. You can’t understand somebody’s heart in a DM.”

Every season brings a new city, and when we talk about filming in Philadelphia, Tommy lights up. “One thing about Philly? They’re coming — and they’re coming for real,” he says. “The singles there, they ain’t playing. They’re direct, they know what they want, and they bring that energy.” As for the larger conversation about Black love on TV, Tommy gets reflective.“We get to see ourselves,” he says. “We get to see Black love unfold right there in front of our faces — the ups, the downs, the raw truth of it. That’s important. That’s why people tune in.”

After a decade of matchmaking, Tommy hasn’t lost his sense of humor — or his optimism. For him, love is still worth the risk, the work, and yes, the patience.

“At the end of the day, everybody wants the same thing,” he says, leaning back with a smile. “Somebody who sees you, gets you, and chooses you. That’s what Ready to Love is all about.”

Season 10 may mark a milestone, but for Tommy, it’s just the next chapter in helping singles — and viewers — believe in love all over again. Catch Ready to Love Season 10 airing Fridays at 8/7 c on OWN, The Oprah Winfrey Network — now through the fall. Don’t miss the 150th-episode milestone airing on September 26 at 8/7 c. Trust us, you’ll want to be in the audience for that one.