Cupid’s at work

Southie missed opportunities

Valentine’s Day is the perfect day to make a connection.  In Southie, we would have to guess, there are thousands of missed opportunities to make a love connection. 

Maybe you’ve been stalking a cute bartender at Lincoln.  Or maybe it’s the cute girl on the #7.  Whoever it is, let them know!  What the hell are you waiting for?  He who hesitates is lost. 

We will post your missed connection and let fate happen.  What have you got to lose?

Send your missed connection to Maureen at  Consider her your fairy godmother!

MISSED CONNECTION:  Here are some from last year:

Dear Phil (at least I think that’s your name),

Last year, after we spent the day shoveling our cars out from 2 feet of snow on opposite sides of the street, you left the nicest note on my windshield. I couldn’t take you up on the offer then, but I can now. Are you still up for that drink? Hope so.

Your shoveling buddy,

If you are “Phil” and would like to connect to Sara – kindly email Maureen at 

You'll Also Like

Latest Property Listings

About the Author

Maureen Dahill

Maureen Dahill is the editor of Caught in Southie and a lifelong resident of South Boston sometimes mistaken for a yuppie. Hockey mom, yoga enthusiast, lover of red wine and binge watching TV series. Mrs. Peter G. Follow her @MaureenCaught.


  1. Maureen Dahill says


    Dear Ben from L St T-

    My jacket was returned to the bar… Just thought you’d like to know.


    I win!




  2. #11 Blondie says

    Several women and strangers on the #11 strike up a conversation about the good looking delivery man from Bay View Liquors. Don’t be afraid to chat with your clientele on the streets.


    #11 Blondie

  3. Maureen Dahill says

    Dear Office Crush- 

    I wish I could come out and tell you how big of a crush I have on you. You are my ideal man. I am going to continually invite you to come out in Southie with my friends and I in a very hopeless romantic type of way. Come sunday funday with me at BBG, sing country at the Playwright and keep me warm in line at Lincoln
    Dreaming of you and your 6’5” manliness. 
  4. Maureen Dahill says

    To the Hottest Dog Walker of Southie,

    (Crossed between Ben Affleck & Tom Cruise)

    I often run into you on the streets of Southie walking our neighbors dogs. I’ve even considered trading in my two kids for some dogs just to have you come to my house and walk them. Just want you to know your really good looking and should be a paid male model instead.
    Also-Just wondering, are you single & interested in women(just a small bet- I firmly believe your straight.)fingers crossed

    Dogless & your #1 fan