A Night Out!
Gentlemen, now that you have time to date, you need an outfit. Start with a classic polo sweater; this one is merino wool and only $32.99 from Bluefly. Several other colors are available, so pick one that works for you. Pair this with a pair of flat-front khakis to look casual but still put-together; this pair is $49.99, by Theory, but this is a basic so you can find it anywhere. Just don't wear pleated or tapered pants!
Finish off your look with a pair of loafers, like these by Bass, $53.95 in either black or brown leather, from Zappos.
All of these pieces are versatile and classic, so you can think of them as investments. Come to think of it, you can consider a date an investment too, so go ahead and jump into the stock market.