Will
WILL
knew that taking Bridget to meet his mother, to his childhood home, was a risk. He was aware that, in doing so, he would be teetering a dangerous line. But letting her get to know this extra piece of him, to show her another part of who he was, was way too tempting.
In preparation for today, when had called his mother to let him know he was bringing a guest, he requested the topic of work and careers be taken out of the approved list of conversational topics. In fact, it was his condition for attending the party (not that there was any way he was going to miss it, anyway). He wanted Bridget to know the good parts of him. He wanted her to see that he was not a bad man despite having done many bad things. To her. To his mother. To lots of people.
He wanted her to fall in love with the good sides of him before she realized just how terrible he has been.