Editor's Note: Sid Lipsey is a producer with HLN's Showbiz Tonight.
Taylor Swift's penchant for writing songs about her ex-boyfriends has made her love life the stuff of pop culture legend. But now, fans of the 22-year-old singer are wondering if she's embarking on a new and super-expensive, romantic misadventure with her suspected boyfriend of two months, 18-year-old Conor Kennedy (son of Robert F. Kennedy, Jr.).
Swift reportedly paid $5 million for a Hyannis Port, Massachusetts, home that sits just across the street from the home of Conor's grandmother, Ethel Kennedy.
I don't want to sound cynical, but either Taylor's intentionally trying to sabotage this relationship because she needs one more break-up song for her next album, or she has serious boundary issues. Yes, Taylor and Conor appear quite smitten with each other. And Taylor is said to get along famously with the Kennedy family -- especially Ethel. But plunking down several million dollars to be within distance of the teen you may be having a summer romance with seems a bit rash. From what I remember from my single days, most guys hate clingy girlfriends. And Taylor's real estate venture could come across as a big, flashing red sign of a Stage-5 clinger.
So is Swift moving too, um, swiftly? I posed the question to New York dating coach Tracey Steinberg (full disclosure" she wasn't hard to reach; we've been married for five years). Her surprising answer touched off a heated Steinberg-Lipsey household debate.
"I don't see anything wrong with it," Tracey said.
"This doesn't strike you as clingy?" I asked. I reminded Tracey that she advises clients to take new relationships slowly (i.e., no talking about past relationships on the first date, no rushing into sex and, presumably, no major real estate transactions before your six-month anniversary). "What if a client came to you," I asked, "and said, 'I went on three great dates with this guy, his family's awesome, so now I'm gonna move in across the street from his grandma?' You'd suggest she get help!"
"Not necessarily," Tracey argued. "Taylor buying the house may have had nothing to do with her boyfriend. Maybe she loves the location, the house, the price. And the fact that it's next door to a guy she knows could be a cool bonus when she vacations there."
"And you don't think Conor finds this a little bit too 'Fatal Attraction?'"
"You may be too old to remember what it's like to be a teenager in love," Tracey responded with a little too much glee for my taste (I'm 10 months older than Tracey, and she never lets me forget it). "Conor's probably ecstatic to have his girlfriend so close by. Everyone thinks their first love is going to last forever."
I pounced. "But most relationships at that age DON'T last!" I said. "What is Taylor supposed to do if, heaven forbid, they break up? Returning an ex's T-shirt or changing your Facebook relationship status is one thing. Unloading a $5 million reminder of your failed relationship is something else."
Alas, as in debates about vacations, pizza toppings and whether to watch "House Hunters," dating coach/my wife Tracey had the last word on The Great Taylor Swift House Debate.
"Sure, it's possible this won't work out," she acknowledged. "But right now, Taylor has a beautiful new home and, apparently, a great new boyfriend. Whatever happens, I hope she lives her life without regrets."
Well, anyone who listens to Taylor's music knows she has plenty of regrets. And that's exactly why she can afford a $5 million vacation home in Hyannis Port. She may be unlucky in love, but Swift is obviously doing something right.