PEOPLE has an exclusive sneak peek at Wednesday’s Real Housewives of New York City, where Tom and Luann come face to face with one of his ex-girlfriends.
The awkward moment happens at a party at Ramona Singer‘s newly redecorated apartment. There, Missy — a friend of Singer’s who also used to date Tom — greets the happy couple.
“You guys met once before, I think at the Regency,” Tom says, introducing Luann to Missy.
Indeed they had — though as Missy explained in a previous episode, their first meeting took her by surprise. At the time, Missy claimed she was still dating Tom and had no idea he was engaged to Luann.
They seem to be on good terms now, with Tom telling Luann: “She’s nice, she’s so happy for us.”
But when Tom and Missy chatted, she couldn’t help but give the 50-year-old lifelong bachelor a jab about his new wedding ring. “What is on your hand? she asks him.
“Tell me about it,” Tom jokes back. “I’m getting used to it. It’s like a dog with a collar.”
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Later in the clip, Harry Dubin — a longtime RHONY guest star who previously dated Luann and Sonja Morgan, and was previously married to former New York Housewife Aviva Drescher — grills Missy about her relationship with Tom.
In their chat, Dubin references a claim Missy had previously made saying she and Tom had kissed after his engagement.
“So he dragged you into the bathroom at the Regency? And you kissed him back?” Dubin asks.
Missy keeps her mouth shut. “I don’t know,” she says. “I don’t want to get involved in all of that. And she’ll come after me. I’m scared of that look. With like daggers in the eyes.”
She may think that, but Luann doesn’t appear to be bothered. “I’m still friends with my ex husband,” she confesses to viewers. “I totally understand how you can be friends with your exes. I think it’s a healthy thing.”
The Real Housewives of New York City airs Wednesday (9 p.m. ET) on Bravo.