Silent Knight

I'm thinking I should wait until after Christmas to break up with my girlfriend of two years. She is planning on accompanying me to my family's for the holidays and otherwise has no place to go. (I'm picturing her home alone, maybe calling her stepbrother she talks to once a year.)

--Not Jolly

When your thought is "I think we should start seeing other people," it isn't supposed to mean making your girlfriend spend a week with your grandma and 62 of your closest relatives. Although you're trying to be kind, delaying your breakup is the wrong thing to do. You break up with somebody as soon as you know, which means they can lick their wounds and get on to somebody who does want them that much sooner. (There are exceptions to the immediacy rule, like if it's two days before your girlfriend has finals or if somebody's just died and she's on her way to identify the body.) Just think how what you're suggesting could play out. In the weeks before Christmas, she'll likely sense that something's not quite right. She'll gnaw endlessly on this with her girlfriends, and they'll come up with the perfect solution...Santa lingerie! When you finally end it, she'll likely drag out of you that you weren't really feelin' it -- starting around Halloween. So, besides the painful emotions that accompany any breakup, you'll be giving her the gift of humiliation as she replays the mental video of herself prancing around in a Santa hat and jingle bell pasties...on what turned out to be the biggest chopping day of the year.