Andrea Moore woke up on November 5 with nothing to do.
She had not felt that way in 40 years.
After college, she had spent over 20 years in financial services, with firms like UBS, Deutsche Bank and Salomon Brothers.
Returning to Westport, the 1984 Staples High School graduate was elected to the Representative Town Meeting (RTM). Then came the Board of Finance, including vice chair. In 2021 she ran with Jen Tooker, and became 2nd selectwoman.
Moore was an active civic volunteer too. She was president of the Child’s Place preschool board, Saugatuck Elementary School PTA and Staples Tuition Grants. She served on the Westport Weston Family YMCA board of trustees, and the National Charity League’s local board.
But on Election Day nearly 3 months ago — running for re-election — she and 1st selectman candidate Don O’Day suffered a resounding defeat.
He became 3rd selectman. She became unemployed. (Though the $2,000 stipend for 2nd selectperson may not really qualify as “employment.”)
Andrea Moore, at Studio Café.
Moore was so focused on the campaign, she had not thought about next steps if she lost.
In the weeks since, she’s taken time to figure out what’s ahead.
One thing she is not thinking about is “what if…”
Republicans nationwide suffered losses in November, from the governor’s mansion to town boards and commissions. In Connecticut alone, 30 cities and towns — including Westport — shifted from Republican leadership to Democratic.
“We worked hard. But nothing Don and I did differently would have mattered,” Moore notes. “There are masses of people who never would have voted for Republicans.”
Andrea Moore and Don O’Day, on the campaign trail.
The moment the first RTM district’s results came in, Moore knew they had lost. That chapter in her life was over.
Two months earlier, Moore’s youngest of 3 daughters began her first year at Emory University. The campaign was already in full swing.
The result: Moore never had time to deal with “empty nest syndrome.” Then came the holidays, and a trip to Australia, where she had spent a year during college.
Now, in January, she has time to do things like clean closets. But she knows she’s not the type to spend “the next 30 years” doing that.
“It’s a relief to not wake up thinking about “the community gardens, and the comments on ‘06880,’” Moore admits.
Still, there are many aspects of her most recent role the misses.
The 2nd selectperson has no specific role, beyond serving on the Select Board. Tooker delegated important tasks to Moore, including vetting potential members for all boards and commissions.
There was a large backlog of appointments, after COVID. Then — in response to a challenge to the makeup of TEAM Westport — the town reassessed the membership of all appointed bodies.
“I got to meet so many people I never would have known,” Moore says. “I was able to help them find a place where they could put their talents and passions to work for the town.”
She met others too, like Y’s Men members, whose friendships she now cherishes.
Selectwomen Jen Tooker and Andrea Moore, at a Wreathing for Community event.
Another highlight: Helping raise — very quickly — the funds and volunteers to light the Cribari Bridge in 2024, when it seemed the longstanding holiday tradition would end.
Tooker and Moore had an excellent relationship, professionally and personally. Moore acted as advisor to the 1st selectwoman.
She also acted as a buffer, an ambassador, and a conduit.
The role suited her well. “I had an impact. But I wasn’t on the firing line,” Moore says.
Now — as Moore assesses her next challenge — she is moving slowly and deliberately. Whatever she does, it must align with her interests and skill sets.
She already said “yes” to the Westport Downtown Association. With her deep knowledge of the town, its operations and its people, she’s eagerly joining their board of directors.
“It’s a very good group. They put on great events,” Moore says. “They support local business, and they’re expanding.”
Andrea Moore, at the 2025 Downtown Westport Association’s “Fashionably Westport” show. (Photo/Dan Woog)
Beyond that, she asks herself: “How can I use 20 years of relationships and knowledge in this town, to help create something good?”
One thing she has no time for: people who pat her solicitously on the arm and say, “I’m so sorry for you.”
“I hate that,” Moore says. “I was sad we lost. But now I’ve got a great opportunity to move ahead. I look forward to whatever comes next.”
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gain: How would any newcomer know the answers? Even those motivated by a particular issue — Long Lots School, say, or bike paths — may have only a vague notion of the RTM’s role in our town.
