So I met this guy at work (he doesn't work there, but was doing some work for us). We got to talking while waiting for my boss to show up and we made a bet about something (whoever lost would have to buy lunch sometime). As he was leaving, he said that he hoped one of us wins the bet so we can do lunch.

We exchanged emails later that day (still work-related) and in his last email, he wrote that regardless of how the bet went, we should still go to lunch and he'd buy.

I got the vibe that he might like me (reminds me of Seinfeld - where the guy made a bet w/ Elaine so he could take her to dinner). He's nice but I'm not interested... Assuming he contacts me again (he might, for work-related stuff) and mentions the lunch, should I go? I don't think having lunch would be horrible (though I would prefer not having to go). Besides, there's a possibility lunch is just lunch (not a date) and we did make a bet that loser buys lunch.

If I lose the bet (which, the way things are looking, I will), should I pay? Just to make sure lunch is the wager and not a date...

I say go for it, why not? He could turn into someone you like.

Well you have the whole lunch to decide, if you don't like him like that.. pay if not.. let him.

I don't think you should go do something that you don't want to do are aren't comfortable doing.. I wouldn't go to lunch if you're completely interested... you don't want to lead him on.. but if you think there might be a chance that you could like him, then try it out..

If you will be uncomfortable during it, don't go
However, if you are looking for a friend, perhaps go and see what happens

Get a group of your co-workers together and go to lunch, then make him buy. Then you will have that group situation where the two of you are not alone.

First, go to lunch with him. You should always take the opportunity to get to know someone better. Who knows where it could lead... a new friendship, a career opportunity...

Second, a bet is a bet. If you lose, pay up.