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Breakup Girl » Broken Heart Bob
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December 7, 2012

Age: Mr. Nice Guy meets Ms. Older Woman

Filed under: Advice — posted by Breakup Girl @ 10:15 am

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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.

– Broken Heart Bob

BG helps an old friend after the jump!

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March 27, 2008

Broken Heart Bob is back!

Filed under: Advice — posted by Breakup Girl @ 3:37 pm

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And now a word from a BG VIP: It’s Broken Heart Bob, the original Loft-Builder!

When we first meet BHB, he asks, nicely, how he can be a nice guy without being The Nice Guy. The guy who women flock to… for help with odd jobs. You know, the guy whose shoulder women cry on…about other men.

Several months after that, he’s back, and he’s crushing on someone 11 years his senior — though at least, thankfully, not expressing his feelings by offering to drive her to the airport or move her piano.

Then: Another missive detailing a massive dating drought in which dry conditions also help set an old flame alight. Which would be hot except for the part where she’s married to a doofus. And now he’s got a tattoo: a tattoo of the earth on his shoulder. The world! On his shoulder! Oh, the weight! Oh, Broken Heart Bob!

And now! BHB writes from Africa! Turns out our man has joined the Peace Corps. In other words, he is building the world a loft, in a good way. Here is his latest missive, plus a bit of a pep talk from BG. (Note: This response from BG to long-time VIP/FOBG BHB is an extra-special VIP case. Please send your requests for advice to my alter-ego at AskLynn@match.com) Feel free to add your comments as well!

(more…)

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