6 Apr I used to be the kind of girl who always thought that guys should pay on dates. When I was in my twenties, I'd commonly give my friends advice. 23 Mar Even though gender doesn't really have much to do with who pays for a date these days, most guys will still offer to pay for you on the first date. 26 Feb Ahhhh the age old question of “who should pay on the first date?” It's a minefield for the modern dating man. Try and do the gentlemanly thing. 8 Mar Back in the olden days, the dating game had "rules" for straight couples to follow. One of those all-important rules? Men paying on dates. “Really, that's just not fair. I always pay my share the first time I meet a man.” ' Janine' said this after I suggested waiting for the man to pay for dates, and then. 29 Aug the Roaring '20s birthed modern dating as we know it. The invention of dating replaced "calling," as we discussed in A Dating Tradition Worth.