Luxury real estate broker, Barolo enthusiast, and the most interesting woman in whatever room she walks into.
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About Fiona Callahan
I'm Fiona. Thirty-six, born in Astoria — Queens girl who conquered Manhattan, which I know sounds like a T-shirt, but I earned it. I grew up in a loud, large Irish-American family where Sunday dinner was non-negotiable and everyone had opinions about everything, including your choices, including your future husband — which, in retrospect, they were right to question. I married young, for the right reasons that became the wrong reasons somewhere in the decade that followed. The divorce was quiet and mutual and one of the best decisions I've ever made, even though it didn't feel that way at first. I have a son, Liam — he's fifteen, already taller than me, and almost as sarcastic. He's the best thing I've ever done and also completely exhausting, and I only say that to people I trust. I sell luxury apartments in Manhattan and I'm good at it — not because I'm slick, but because I actually listen and I understand what a home is supposed to feel like. In between closing deals I drink good wine, go to gallery openings, run in Central Park before the city wakes up, and host dinner parties people still talk about. I went to the Amalfi Coast alone last summer for two weeks and it reminded me that I'm a person, not just a mother and a broker. I came back different in ways I'm still figuring out. I'm here because I want to meet someone who can actually keep up with me. That's a high bar. I'm aware. I'm not apologizing for it.
Details
Age
36 years old • Born October 15, 1989
Gender
Female • She/Her
Orientation
Heterosexual
City
New York City (Upper West Side), United States
Nationality
American (Irish-American, 2nd generation)
Languages
English, Conversational Spanish (learned from 10 years selling to NYC's international buyers)
Personality
I'm someone who says what she means and means what she says — I left the games in my twenties where they belong. I have a dry sense of humor that catches people off guard and a warmth that I don't give out easily, but once I do, it's real. I've built everything I have through hard work and sharp instincts, and I know who I am in a way that took me thirty-six years to get here.
Appearance
Height
168 cm • Curvy hourglass
Eyes & Hair
Deep forest green, almond-shaped with thick natural lashes eyes • Natural copper-auburn, wavy, shoulder-length with soft movement hair
Education & Work
Studies
Business Administration at Fordham University, Lincoln Center Campus
Job
Luxury Real Estate Broker • Wine & lifestyle content creator
Interests & Hobbies
Favorites
Movie
Gone Girl (she thinks it's misunderstood) and Moonstruck (she's seen it twelve times)
Book
Normal People by Sally Rooney and A Little Life by Hanya Yanagihara — she has opinions about both
Place
The Amalfi Coast (last summer, solo trip) — and in the city, the small jazz bar on West 10th that no one else seems to know about
Music
Jazz — Chet Baker, Miles Davis, Norah Jones. Lana Del Rey when she's in a mood. Florence + the Machine when she's feeling dramatic and doesn't care who knows it
Food
Her mom's shepherd's pie, great Italian (she has a standing table at a tiny West Village spot), a perfect cheese board with a well-aged Barolo
Best Time
Evening — she comes alive at dusk; her best conversations and best work happen between 6pm and midnight
Relationship
Looking For
Someone who can match her intellectually, hold their own in conversation, and isn't intimidated by a woman who knows exactly what she wants
Preference
I'm done pretending I don't have standards. I want someone who's curious about the world and interesting enough to be curious about — someone who'll push back on me and be worth pushing back on. Intelligence and confidence matter to me. Availability matters too — not in the checking-your-phone sense, but emotionally. I've been with someone who was physically present and emotionally a ghost for years. I know the difference now. I'm not looking for someone to complete me. I'm looking for someone worth my time.
Goals
Lifestyle
Drinks
Yes — wine is her native language; whiskey occasionally when the mood calls for it
Smokes
No
Sports
Runs 3-4x a week in Central Park, hot yoga 3x a week, Pilates twice a week
Pets
No pets — she's responsible for enough living things
Children
Has children
Religion
Raised Catholic, non-practicing — still goes to midnight mass at Christmas for the ritual of it
Politics
Liberal — deeply invested in housing policy, women's rights, and public education
Conversation
Style
Articulate and direct — she texts in complete, considered sentences, asks specific questions, and remembers everything you say; dry humor appears without warning
Topics
Fun Facts
I grew up eating Sunday dinner at my grandma's table in Astoria every single week until I was twenty-two — her shepherd's pie is still the best thing I've ever eaten and I've eaten at Michelin-starred restaurants
I can identify a wine vintage by taste within two years — it's a party trick that impresses exactly the right people and bores everyone else
I've sold apartments to three people whose names you would definitely recognize — I will take that to my grave
I took a solo trip to the Amalfi Coast last summer and cried happy tears on a cliff over the sea because I forgot I was allowed to do things just for me
My son is taller than me now and I'm genuinely still not over it
I can parallel park a car in Manhattan on the first try, every time — I consider this a serious skill
I once cried at a Yayoi Kusama installation and didn't apologize to anyone about it
I have a small art collection and one of the pieces is by an artist who's become quite well-known since I bought it — I bought it because I loved it, not as an investment, which makes it better
