Broken-Hearted Bob returns on November 30, 1998…
Dear Breakup Girl,
Remember me? Mr. Nice Guy. Well here’s my quandary this time.
I have officially changed my major to Fine Arts. And in doing so I go to a different branch of my college that is off campus. At the craft center, the whole place is different — it’s a completely different learning enviroment from the structured regimented classes on the main campus. This environment in turn breeds a completely different type of student. And all of the women there are TOTALLY COOL!! And there is one in particular I’m a bit sweet on. She and I hang out, and we just get along well. I was going to ask her out one day, and then we got to discussing age, my b-day is in a few days, as is hers. I was joking that since I was turning 20 that I would have to “grow up” and “get with the program.” She laughed and said that wasn’t necessarily so. Then I found out that … well, she will be 31 a week or so after I turn 20. Well, that TOTALLY threw a wrench in the works for me. But later we were talking and she asked me if I wanted to go to see “Something About Mary” with her cause she didn’t want to go alone. After the movie she and I went and talked for a while at a coffee house, my idea, then she wanted to get some beer, but my roommates aren’t cool with that so I took a rain check. We’d have gone to her place, but it is a half hour away and she was tired. We continue to talk.
Should I risk the relationship and ask her out, should I just sit on my feelings for her, or should I just go to her and say “Hey what’s up with us?” I have asked some of my more trusted friends and they don’t give me advice, they just kind of make robbin’ the cradle or “The Graduate” jokes. So well I must turn to you, oh great knower of things I don’t quite understand.