Illustration: Emma Erickson

Welcome to “Apartment Department,” Curbed’s advice column by Clio Chang. Join us every other Wednesday for questions about making peace with noisy-sex neighbors, the nuances of roommate fridge etiquette, and whatever else you might need to know about renting, buying, or crying in the New York City housing market.

Got a problem? Email clio.chang@nymag.com.

Dear Apartment Department,

I want to have sex with my landlord. I’m a woman who lives in an owner-occupied building (there are six apartments), and the owner who lives there happens to be newly divorced and hot in an older-guy way. We flirt a lot, which started innocently when I first moved in but seems to have ramped up a bit. If I take things further — with a fling, or who knows, even by dating the guy — am I ruining my life? Or am I unlocking a possible pathway to domestic bliss and possible free rent if things get more serious? (I honestly really like him.)

Sincerely,

Landlord Lover

Dear LL,

As someone who is categorically averse to chaos (which is why I write a real-estate advice column, not a dating-advice column), my initial reaction is to stay away. The potential for mess here is high — there are millions more ways this could end badly than it could end well. You could have a serious relationship, break up, and then have to watch your ex-boyfriend landlord bring his new dates home — which might make you want to move out. In the worst-case scenario, your relationship ends acrimoniously and your ex-boyfriend landlord tries to harass you out of the apartment or raises your rent by $1,000 for fun. Even if you have a fling and it simply peters out, you’ll still have to text him when your toilet breaks. Have you seen the price of listings lately?

However, I also understand that dating in New York City is hard and chemistry is chemistry. All the better if it ends with free rent, I guess. So I asked Shira Etzion, a couples therapist who has much more experience than me in these matters, what she thought. While Etzion cautioned she would need more details to actually advise someone in this scenario, she didn’t write it off wholesale. If you feel secure in your housing options and financial situation overall (so free rent is a fun bonus here, but not a necessity) and are ready to take responsibility for whatever happens, then why not? “I personally think it’s worth the risk as long as there are no red alarms in your body saying otherwise,” Etzion said. “Just the idea on paper that it happens to be your landlord, I don’t think is enough to not listen to your heart.” Okay, that’s romantic.

Janis Spindel, a professional matchmaker whose clients are extremely wealthy men (her services start at $75,000), had a piece of old-fashioned advice: Don’t sleep with him right away.  “Otherwise he’s just gonna think she’s a ho,” Spindel said. While I don’t necessarily agree with this sentiment (hos’ rights!), it might actually be a good idea in this specific case. You guys live in close proximity and there’s a bit of a power differential — it’s probably better to get to know him a little before you ramp things up. Is he a vindictive guy? Does he hold grudges? Is he even single? Spindel also cautioned that you shouldn’t have any grand expectations before going into it. (Or as she put it: “Big deal, he owns a six-unit building.”)

There are also some practical matters to figure out before dating your landlord. The first would be to figure out if your apartment is rent-stabilized (your building size is right on the cusp but could qualify) or if your building falls under the Good Cause Eviction law (the law only applies to landlords who own more than ten units, but you can poke around and see if he owns multiple buildings, which is a sort of odd version of internet-stalking your crush, I guess). If your apartment is protected under either of these laws, you are “entitled to a renewal whether or not the relationship works out,” says tenant lawyer Jennifer Rozen. Even if you are a market-rate tenant, you could technically file a retaliatory-eviction claim if your ex-boyfriend landlord doesn’t renew your lease, but that would only grant you another year in the apartment, per Rozen. You can also search your building on Who Owns What to see its history of eviction filings, so you know if your landlord is the kind who might try to boot you out. If you embrace the chaos, at the very least you should be well-informed.

If you decide to go for it, write back, obviously. Now we’re all invested.

Have a question for the Apartment Department? You can send it to clio.chang@nymag.com.

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