I really have to put myself out there, being a male and 39, so I have to send out messages to anyone I see with potential. Rarely do I get anything back and only go on a few dates a year, but now I have 2 dates almost one after the other, 1 or 2 days apart. Is it wrong to do that? I see a lot of potential in both, though both are 20 minutes and in the city, while I'm in the suburbs. I might even want to give both 2nd dates to make sure.. but it just seems odd doing this. If the first one goes well, what do I tell the other? I have a 2nd date with someone else? It'll be hard enough driving and parking in the city... in Chicago it's like $20+ to park somewhere. Logistically I'm not sure what to do here. Both are scheduled on the weekdays. On the other hand, my 6 year long (now ex) and I are still hanging out like nothing changed a year ago, and we see each other every weekend and Wednesday until we find someone else right for us, that's our arrangement. She's al...