squirrelatemycookie

Had an interesting conversation with a Baby Boomer the other day. I brought up that I work 3 jobs, wealth management clerk, restaraunt manager and production editor for a local theatre group. He said "Good lord, son. You're gonna work yourself into an early grave. Just keep some job and you'll be fine." Then I look at rent costs and the yearly inflation rate. Seems like this is the minimum needed now. How do I tell him that it isn't 1995 anymore?

As a guy, here is what I think would be likely to ease me into being receptive to you eventually opening up about those feelings. I'd say just start with light conversation and ask them casually if they would be interested in seeing a movie, getting lunch or some other casual hang out activity. After a few times if you get those meeting arrange, then follow with telling them how you like hanging out with him. Then from there after a while, you could ask about if they are single, plans for the future. Then you could formally ask him on a date.