I also think that the conversations between Doug and Claire on their dates was also quite suspicious.  How could Claire not have had a clue as to who Doug really was, given that Doug seemed overly interested in the details of the robbery when Claire related it to him, and  when Doug began schpeiling off to Claire on their date about his supposed knowledge about the FBI, the Criminal Justice system overall, and Wit-Sec, that he supposedly obtained through watching various fictional TV programs?  Claire, imho, didn't think, and was woefully short on common sense.  Another woman wouldn't have been so quick to accept a date with some stranger of a guy who'd followed her into a local laundromat, would've been quicker to pick up the hint as to who Doug really was, and sought help from the FBI, in order to extricate herself from a potentially dangerous situation.  

Contrary to what most people believed, Doug MacRay wasn't the good, decent guy that he came off as.  He acted like a pussycat towards Claire, exploiting her all the while in the hopes of going back to prison, knowing that the Feds were rightly on his trail, while acting like a complete jerk towards Krista, who Doug also exploited, only for sexual means.

The scene where "Jem" crashes Doug and Claire's lunch date, with the conversation, is also quite suspicious, and here's another instance where Claire could've/should've picked up the hint about who Doug really was and what he was up to.  When  Jem starts dropping hints about  "Doug being a real work-a-holic", feigning concern and interest about the Cambridge Merchants Bank (where Claire was the manager), and the fact that Doug put his hand over the Fighting Irish tattoo on the back of Jem's neck so that Claire couldn't incriminate them, that, too, should've been a red flag for Claire as to who Doug really was.    Doug and Jem were probably laughing up their sleeves at Claire's extreme gullibility and naivete.  

Sure, I realize that  Doug decided to trail Claire to see what she knew, at least in part because Jem would've been only too happy to do Claire immediately, but Doug was attracted to Claire, at least in part because he saw her as someone who he could exploit for his own selfish motives;  to avoid going back to prison.  That's why he supposedly wanted Claire to go to Florida with him, but that didin't work, and there's no way that it could've worked.  Sooner or later, Doug would've been hunted down by the Feds, caught (perhaps violently), possibly gunned down by the law, or sent to a Federal penitentiary for a long, hard time.  Claire would've ended up in the line of fire, and not been safe.  

Krista was also quite resentful of Doug for having broken up with her and spurned her for Claire, the bank manager, but she retaliated against Doug by ratting him and his friends out to the FBI about the upcoming Fenway Park heist that they were about to pull off.  The reasons go a bit deeper than that, however;  When Krista is visited by FBI Agt. Frawley after ending up in MGH emergency room due to an injury to an OUI-induced auto accident, with her daughter in the front seat, she is threatened with the loss of Shyne, so that was also the reason that Krista ratted Doug and his men out to the FBI about the Fenway Park robbery.

I also don't think, however, that Claire had any intention of going away with Doug.  She was just sort of playing along with him in order to play for time, because she may or may not have had some feeling at that point that Doug was into some sort of wrongdoing, but couldn't put a finger on what it was.  

The fact that Doug also purchased Claire an expensive diamond necklace from Tiffany's is also quite suspicious.  How could Claire not have had a clue at this point who Doug really was and what he was up to?  There's no way, imho, that a white workingclass Charlestown Townie could afford such an expensive gift for any woman in his life!  

FBI Agt. Frawley and Ofcr Dino Ciampa (an ex-Townie) were both suspicious, not only of Doug, but of Claire at that  point, thinking that she knew more about what happened when Doug and his men robbed her bank at gunpoint than she was letting on.  The fact that Claire was so evasive when Frawley interviewed her was also quite suspicious, as well.  She denied having seen anything that could identify the robbers to  Frawley, for example (i. e. the tattoo that she saw on the back of Jem's neck).  

Agt. Frawley had Claire's phone tapped for a reason;  he suspected that she knew more than she let on about the events, and was caught, red-handed, in a relationship with Doug MacRay.  When Frawley comes to Claire's Charelstown condo with photos of the suspects in Claire's bank robbery,  she adopts a nasty attitude towards Frawley, not only denying that she was traumatized by  what Doug and his men did to her (Claire quit her job as a bank manager as a result), but she was angered about having been caught in a relationship with Doug, which she shouldn't have been in, to begin with.  I really do wonder...how unsmart can somebody get?  

It's also clear to me that Claire Keesey is the victim of the "Stockholm Syndrome", because she not only considers Agt. Frawley as the enemy, but she refuses to sever all contacts with Doug after learning who he really was, and what he was up to.

At the beginning, when the FBI and ofcr Ciampa explain something about Doug MacRay's life (his wash-out as a pro-hockey star, and ultimate following his father's footsteps and becoming a professional criminal), it was very clear that he wasn't the nice guy that he came off as.

 The fact that Doug lied his way into Claire's heart, pretending that he was an upstanding, law-abiding citizen, when, in fact, he was anything but that indicates the kind of person he really was;  a sociopath who exuded a lot of charm.  The fact that Doug got Jem to help him assault, beat up and permanently cripple two guy who'd harassed Claire by throwing bottles at her when she'd been foolish enough to walk through a housing project by herself also indicates that Doug was more like his father than he was willing to admit;  a man of unprovoked violence.  Doug didn't beat up those guys in self-defense.  It was revenge, plain and simple.

Pete Postlethwaite was somewhat believable as "Fergie" the Florist, as well.  It's too bad that he died so soon after "The Town came out.  When he threatened to "clip Doug's n*ts like he'd clipped his daddy's", it was clear that Fergie had sterilized Doug's father, in both the literal and the figurative sense;  he'd injected Fergie with a female hormone to shut off the production of testosterone (like they do to horses), and then got  Doug's mother hooked on heroin, and caused her commit suicide by hanging herself.  

When Doug goes to Claire's apartment to explain what he did, that he'd meant to tell her what he was up to on the night that he and Claire had made love in her bedroom, Claire refuses to believe him, and angrily kicks Doug out of her apartment.  Why didn't she do likewise when he came to visit her in her garden and tell Doug pointedly  not to come around and bother her any more?  That's kind of beyond belief, but she could've and should've.  

Doug hides the money bag full of stolen blood money in a small hole in Fenway Park, and then sneaks back to town and hides it in Claire's garden, where Claire sees it with a note telling her to do whatever she wants with it, that he's leaving Boston, and that he'll "see her again, this side or the other", which is a euphemistic way of saying that they won't ever meet again, contrary to what many, if not most people believe.  

Fergie also supposedly threatened to do Claire in, so, due at least in part to that, and partly to avenge the destruction of his family, he goes back to Charlestown after the Fenway Park Robbery, and after his 3 buddies in crime were killed in a shoot-out between them and the law, enters Fergie's flower shop and guns down Fergie and his henchman, Rusty, out of revenge.

Another thing that I really didn't like about "The Town" is the fact that Doug ultimately escaped justice and became a real fugitive from the law, courtesy of Claire, after he telephones her and apologizes to her for what he'd done.  Claire then tips Doug off with a "sunny days" code about the Feds' presence in her house, and Doug ultimately gets away to Florida, scott-free.  

Will Doug really be scott-free, however?  Nope, not really.  Doug skipped town for Florida without Claire for the following reasons:

A)  Somehow Doug must've known that his days of hiding out in Florida were numbered, and that the Feds would eventually catch him.

B)  Doug was hoping to avoid going back to prison.

C) Doug was also hoping to throw the FBI, SWAT and the cops off of his trail.

D)  Claire wouldn't have been a bit safe;  she would've ended up in the line of fire.  

I feel that had Doug really wanted to redeem himself, he would've immediately stopped robbing banks and armored cars, and found honest means of getting the funds for the restoration the the local ice rink for the kids in the community, and did all kinds of good stuff in the Charlestown community to raise the money for the renovation of the ice-hockey rink himself, instead of using Claire as sort of a go-between, to spend stolen money (which wasn't hers) on the renovation of the hockey rink.  

The fact that Claire refused to sever all contacts with Doug even after learning who he really was and what he was up to indicates that Claire was not such an honest person either.  Imho, Claire should've either been criminally prosecuted herself, or at least put on probation for being an accessory to Doug MacRay's crimes (which, imo, she most definitely was!), and receiving stolen goods (Doug's blood money.).

The Town was also unrealistic, in that Doug and his men would've probably killed, or at least injured Claire, and she wouldn't have gotten off so easy, either, had she survived.  

I do not like the overall message that The Town conveys to me, personally:  

A)  That anything goes, as long as the perpetrators can get away with it.

B) That it's okay to be an accessory to a person's crimes, to make utter dupes of law-enforcement people whose assignment is to bring criminals like Doug MacRay down,  to try to protect somebody who's clearly a professional criminal with an extensive criminal record of violent crime(s), to accept gifts, including stolen money from him, and to spend stolen money that wasn't hers, on the renovation of a local hockey rink, instead of finding more honest ways to obtain that money.  

C)  That putting the very lives and safety of innocent bank employees and customers, and law enforcement people alike at risk is perfectly legitimate, that it's okay to stalk someone like a predator, hunt them down, and take advantage of their gullibility and the fact that they've been traumatized by their crimes.

All told, I am not a big fan of "The Town", and I think that it could've/would've been better with a different cast, and a somewhat different story, but that's my take on it.  

Thanks for letting me ramble, and for listening.