The 20 Worst Decisions You Can Make in Boston

You make great choices most of the time, but they can’t all be winners. There's times when, for some reason, the synapses in your brain misfire and suddenly you're on an expressway to Regrets-ville (pretty sure it's in the 'burbs). Stay strong and beware these 20 terrible decisions in Boston.

1. Cruising Storrow Dr in your moving van

It’s a tried-and-true formula: tall truck + low clearances = you’re stuck. You'll be reminded every second that you're screwed by the the angry drivers trapped behind you cursing your existence.

2. Wearing Yankees gear

This should be a no-brainer, lest you want to receive an errant beanball or beanbottle. Now, a “Yankees SUCK” t-shirt, those are always in-style and hilarious.

3. Taking the Green Line when the Sox have a home game

Speaking of the Sox, sure, you have an undying affection for the hometown team, just not when you're coming from Downtown and the first pitch is at 7:05. Avoid the beleaguered Green Line on game days, and even non-game days.

4. Driving Downtown

The streets of Boston were formed by meandering livestock back in the day and therefore are not very car-friendly (not even horse and buggy-friendly). Oh, and good luck with parking.

5. Driving anywhere, for that matter

This is a dicey proposition at best within the 495 loop, which pretty much defines “soul-crushing futility” during rush hour.

6. Mouthing off to the wrong person in Southie

No amount of liquid courage will save you during a Southie bar fight, at best dulling the pain of that shiner and freshly damaged ego. Good Will Hunting leaves out the part where Will waits outside the Dunkin' Donuts to snap college boy's legs.

7. Not being a regular at your neighborhood bar or restaurant

That would be just lazy and sad. Head down to your local joint, pick a bar stool, and meet Crazy Tommy. He’s harmless (he's on his meds, right?). Then order a shot and a beer. 

8. Not being prepared for winter

You’re going to need a puffy coat and at least two shovels for starters. Front-end loaders are optional.

9. Forgetting about street cleaning

“You will be tagged and towed.” So say the robot truck voices as they sweep your ‘hood. Turns out they’re serious… you WILL be tagged and towed. Go figure.

10. Owning a car while living in the North End or Beacon Hill

The streets in those parts of town are a hot mess. And narrower than most standard vehicles... and some bicycles.

11. Going to “bad decision” bars

Good decisions turn bad at two minutes past tequila, and certain bars are notorious for enabling that process. You know which ones they are.

12. Waiting for any bus

They are as elusive as Bigfoot and LeGarrette Blount. Even those MBTA tracker apps have given up all hope.

13. Not having a Southie St. Paddy’s Day Parade party to attend

Leave the fire trucks and Star Wars cosplayers to the nanas, kids, and assorted goons. You deserve a friend-of-a-friend’s roof-deck shindig complete with session beers and a bird’s-eye view.

14. Trying to find face value tickets for Sox, Pats, Bruins, or Celtics games

A fool’s errand. Not. Gonna. Happen.

15. Getting a beer at Fenway

Now that you've overpaid for that scalped bleacher seat, it is not the time to waste two innings in line for an overpriced, undersized beer.

16. Not getting a Fenway Frank at Fenway

Why wouldn’t you? You’re at Fenway and they are delicious.

17. Swimming in the Charles

This might be tempting during late July/early August, but the Charles is all murky with… umm… murk. Gross.

18. Expecting cyclists to behave properly

They won’t. The oh-so-entitled two-wheelers will zip by you in the crosswalk… even if you have the go-ahead from both the blinky walky guy AND that weird cowbell noise.

19. Sitting on the Esplanade during the 4th of July celebration

You will need to arrive on July 1st and you won’t make it out until July 8th. Bring some snacks. Wisen up and sit on the Cambridge side.

20. Hanging out at Faneuil Hall

You must have just moved here.

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