Pat Healy should have been with Mary.
Pat was the only one who genuinely fell for Mary. He fell for Mary while getting to know her, albeit as part of his job.
For Ted Mary was just a high school crush. Hiring a private investigator to stalk her 13 years later is beyond creepy.
For Woogie, Mary was the ex girlfriend he couldn't move past.
For Norm, she was that woman who was way out of his league.
For Bret, things just couldn't work out so they parted with dignity.
Pat is the only person who didn't cross the line when wooing Mary. Therefore, he deserved to be with her, not Ted. Ted really was the biggest stalker of them all.