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.