Is it time to move to Boston?

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Q.

Hi Meredith,

I lived in New England and moved to the South in 2020 to take care of my elderly mom (my father and only sibling had previously passed away).  

I started a relationship with a woman from another country prior to moving South. We got married shortly after my move. Big mistake.

To make a long story short, she scammed me out of a lot of money, and we’re getting divorced. My mother recently passed away in December, and there is nothing keeping me where I am. 

Also, I have a son and two young granddaughters who live in New England, so it would be nice to be closer to them. I work remotely and can live anywhere.

I’m in my early 60s and have always dreamed of living in Boston. I started looking at condos online with a realtor and plan to go to Boston in a few weeks to look at numerous possibilities. My thought is to keep my house down here (golf course) and split the year between Boston and where it’s warm.

My question is whether this is a good idea. I don’t know anyone in Boston, so I worry a bit about making friends and dating. I tend to be more shy in large group settings, but I’m very comfortable in small groups or on a date.  I’m very active; I work out all the time and play golf, pickleball, tennis, etc. I love theater, museums, dining out, etc. I also still have my Celtics season tickets … how I’d love to find a woman who bleeds green and shares at least some of my other interests.   

I could drive to see my grandkids regularly.  What do you think about a guy in his 60s moving to Boston without knowing anyone, the ease of meeting people and making friends, and dating in Boston at my age?  

Do you see any difference if I live in Cambridge vs. Boston? Thanks!

– Thinking Boston

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A.

“My thought is to keep my house down here (golf course) …”

“I’m very comfortable in small groups …”

“.. play golf, pickleball, tennis, etc.  I love theater, museums, dining out, etc.”

I also still have my Celtics season tickets …”

Sir, I think you’re going to be just fine.

If you sign up for three pickleball teams and a few museum tours, you will meet friends your age. You will thrive. 

It might take some time, but you won’t have to be very patient. I foresee a few events and activities leading to a full social life, one that might be sad to leave when the weather turns cold.

Some general thoughts:

  1. 1. Try a bunch of activities, some more than once. Your first guided tour of the Museum of Fine Arts might lead to no new friends. But your second? That could be the fruitful one. Try to pick activities you’d want to do anyway so you’re not miserable. We (the media) are also great for bringing people together. I am always impressed by the lineup at WBUR’s CitySpace, for instance, and I have seen a bit of mingling at every event.

2. Don’t get married again until there’s a great reason. Take your time with that kind of decision. Give yourself many months to adjust to change before deciding that any one person – or any one thing – is the answer to your new version of happiness.

2. Boston and Cambridge are big. I can’t tell if you’re a “foodie in North Cambridge” person, or an “cool East Boston condo by the water” person, or a Back Bay Babe, as we might say at Love Letters.

Stay with your son and take some day trips. I will say: Fenway Park, pickleball courts, and at least three fantastic art museums are all in the same neighborhood, and only a T trip away from the Celtics. Plus, it looks like Time Out Market is staying open.

– Meredith

Readers? Tips for moving to a new place? Tips for splitting the year in two spots? Thoughts on where to move, specifically? Neighborhoods for someone like this letter writer?

Send your own question. Help others wondering the same thing. Use the form – or email [email protected].

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