You love West Side Story though which certainly plays up the kind of relationship you dismiss in your last paragraph above.
Yes, I
do love
West Side Story, but the relationship between Tony and Maria didn't come about in nearly the same way as
The Town's Doug and Claire's relationship did. First of all, Tony and Maria were in their teens (or possibly early 20's), while
The Town's Doug and Claire were at least in their early to mid 30's, and therefore way beyond old enough to know better than to play with fire and mess around with the Feds the way they did.
Secondly, although Tony was an ex-Jet and Maria was the sister of the Shark gang leader, Bernardo, their romance came about amid conflict of two gangs of different racial/ethnic groups (i. e. the white Ethnic American Jets vs. the newly-arrived Puerto Rican Sharks), and they met at a local dance and fell in love.
Thirdly, unlike Doug MacRay and his buddies in
The Town, while the Jets and Sharks in
West Side Story were in conflict over the small amount of turf that was allocated to them by the system, none of the Jets or Sharks were into robbing banks and armored cars at gunpoint, taking people hostage, and putting innocent people's lives at risk just so they could steal money that they had no right to, and they were not being hunted down by the FBI. Nor did Tony rob a bank, a movie theatre, an armored truck or car, or a baseball park and leave a whole bunch of ill-gotten money for Maria so she could do whatever she wanted with it, either.
Also, unlike Riff, Bernardo, and the Jets and Sharks in
West Side Story,
The Town's Doug MacRay and his buddies were
career criminals who were armed felons and fugitives, who were wanted by the FBI. Unlike
West Side Story's Maria,
The Town's Claire, who was much older than Maria, abetted an armed felon and wanted fugitive (Doug MacRay) by lying to the Feds about who he was, in order to protect him, and by tipping Doug off to the presence of Frawley and the FBI when they were right on the verge of catching him, with a "sunny days" code. I also might add that Claire was
not some starry-eyed adolescent who got caught up in the excitement of a first love, and then got herself into a jam because she didn't know what she was doing. Claire was an adult, with a full time job and a decent income, who lived in an expensive condominium, in a
gentrified part of Charlestown, as opposed to a real slum area, who had far more choices than "Jem's" drugged out sister, Krista, and she chose extremely poorly, imo.
Having said all of the above,
The Town and
West Side Story, with the exception of both of them being set in tough, mostly run-down urban areas, were about as different as night and day. There's no other way to compare them.
West Side Story went on to win ten Academy Awards, including Best Picture of the year when it came out.
The Town, on the other hand, didn't win any accolades at all, which says something right there, despite people's annoyance over
The Town's not having won any accolades. Granted, not every good movie wins awards and/or accolades, but
The Town did not deserve any, either.