For example, the other day my officemate invited me out for a snack--we were both working on the weekend--this was the first time that I had been out to a restaurant since committing to ERE (only two weeks ago!). This was a social outing that I didn't have a lot invested in--we're not going to be BFFs--so I didn't feel that weird about just ordering tap water and offering a dollar for the tip (which he refused) at the end. It helped that we ran into a few other people who shared our table and ordered food.
My mental image of Jacob is that he spends a lot of time at home, and eschews most social outings--perhaps he'd like to deepen our understanding of his social life? (not to put you on the spot or anything...

In a place like NYC, which I imagine is probably last on the list of EREs' retirement cities, there are tons and tons of free events--opera, theater, concerts--practically on a daily basis, at least in the summer. For those of us who feel the need for greater cultural/social opportunities in ERE than is offered by an off-the-grid country hut, what's the plan?