dear dredwerkz, is it an insurmountable dating obstacle that someone voted for mitt romney in the last massachusetts gubernatorial election?

yours truly, diehard democrat

helena says:

Flirting with conservatives can be mildly entertaining, so if your dating is still in the realm of nonexclusive grabbing drinks when you're up for a debate, I think that this person would be fine to keep around. But to me, that's a friend, not a boy/girl-friend.

Getting serious with someone whose fundamental beliefs are evil is a bad idea. Politics aren't like preferring chocolate or vanilla. I see it as an irreconcilable difference. Heath is slightly less left than I and even that sometimes makes me want to strangle him.

1. Conversion is a waste of time, unless this person is exaggerating his/her conservatism in order to get a rise out of you. If that's the case, I find it obnoxious, but you might find it fun.
2. Always date within your own league or one higher. You're a Democrat; this person is a Republican. You are too good for him/her.

edward says: I've always believed that you can convert anyone from the dark-side. Of course, this approach takes for granted that you have the time and energy to engage in what could prove to be a fruitless quest. (Be sure to score plenty of free dinner/jewelry/gifts in the process, though, so that you at least come out ahead!) Just remember two points if you want to do it:

1. If you don't convert him/her, leave him/her wanting more. Better to have them think "Wow, that really hot Democrat got away...I wish I hadn't been such an idiot" than "Whew, I'm sure glad I didn't end up with that annoying liberal."

2. They have to convert. If they don't, you don't go out with them anymore.

brad says: I wonder when someone brings this up - is this a first date sort of thing? You know, 'this t-bone kicks ass, but not as much as lyndon larouche'...? And though I don't know who diehard democrat is offhand, I'm willing to guess that it's a 'she' because I can't think of a single woman who would openly mention mitt romney while on a date. But you want advice, so here are my two points:

1. Republicans from 'the other commonwealth' are pretty rare, so they're likely to have a chip on their shoulder about politics. Conversation will be frigging irritating...

2. Time spent converting space monkeys sends the wrong message to the other gender...it basically says that you don't care enough about politics to reward those who use their brains when voting. enough said.