spoiler question


All this time that Woogie's known Healey the "bloodhound", why didn't he just have him track down Mary? Could always tell him that it was for work/insurance purposes. In those circumstances, it's unlikely Healey would have done any kind of "surveillance" (as this was only done to find out if Mary was single), he'd have just gotten an address (and her new name) and that would have been it.
Instead his masterplan is to befriend Ted (who might have moved on himself or might just not be that concerned about a girl he had one disastrous date with 13 years earlier), wait for Ted to become so overwhelmed in his desire to see Mary again that he agrees to use Healey and find her, like some kind of real life battering ram - presumably Mary would then be so grateful to Woogie for revealing the truth about Ted (and Healey) that she'd just fall in to his arms.
Brilliant twist finding out that Dom has been Woogie all this time, but crazy plan from him.

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He was getting Toll House cookies and BJs on the regular; he wasn't looking for anything more, but once he was reminded of Mary, he could not stay away.

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Ted and Woogie were friends and it wasn't part of his plan. He knew about Ted but wasn't trying to stalk Mary with him. He says he feels liberated after hearing Mary is a cow and then a little afterwards he starts getting those bumps. It seems like he was getting on with his life but Ted brought Mary back up and he slipped up by suggesting he hire Healey. Its kind of like an addiction, once he got dragged back into thinking about her it was over.

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thanks for the replies. Maybe they were leaving it up to the viewer to decide how long Ted and Woogie had been friends, how they'd met etc.
Given that, as you say, he only starts with the "love-blisters" upon hearing that Mary's a fox, maybe he was over her until then. And even then he wasn't planning on travelling down with Ted, he only headed down south when Ted was imprisoned, and having travelled that far it made sense to carry on to Miami with him.
It is some co-incidence if Ted and Woogie did randomly become friends....then again given that they're both Mary's type, they'd have maybe had similar personalities and things in common and so hit it off.
I do love the little clues that are thrown out too as the story progresses - like how Dom already knows the "zipper" story, and when Ted questions how, says he was only 2 towns over - as in, he'd have gone to a different but still nearby high school, like Barrington High.

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