Caitlin Healey

Caitlin Healey, 40
Senior Vice President at Cabot Properties

Provenance: I was born in Hampton Falls, New Hampshire, the fourth of five children. I went to college in Boston. I lived in London and Miami, and then came back to Boston.

Boston bona fide: I ran the Boston Marathon in 2007 and couldn’t get a pedicure for three weeks after because of pain and damage. I don’t understand marathon runners, but I am contemplating a run this year with my older sister.

Hobbies: I love the beach. I travel quite a bit. I like tennis, but I don’t play much anymore. And sleeping. Sleeping is my favorite activity, but I rarely get to do it.

Guilty pleasures: I lie to people and tell them I’m fluent in Spanish to impress them, but then I get caught. I love to cook. And I love buying and arranging flowers. I used to sneak into the Flower Exchange every weekend by saying I was a florist. I have issues.

Most harebrained thing you’ve done for love (or lust): Well, lots of stalking. And pretending to love hiking or mountain biking. 

On a first date, you like to: Have coffee or drinks—maybe dinner.

On a first date, what would horrify you is: Drunkenness.

Last time you fell in love at first sight: Probably last night at Whole Foods.

Your worst trait: Indecisiveness.

Most deplorable characteristic in others: Unkindness.

Achievement you’re most proud of: Making my bed in the morning.

Would you ever date someone you do business with: No.

Thing in a potential partner that’s non-negotiable: Kindness.

Meet the next most eligible single»

BACHELORS and BACHELORETTES: Hayley | MarkJosh | Casey | Caitlin | JordiClaudianeJamesChristina | Sam | MattTitiCarolineKitznerElizabeth | GarrettMichael | AlexChrissy | Derek

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