Ask Natalie by Natalie Bencivenga

Should a Guy Be Expected to Foot the Bill on a Date?

DEAR NATALIE: I went out with this guy (we are both 23) recently that I met online. He was totally nice and seemed into me, but it was weird because he didn't pay for my drink -- at either bar. And even the bartender at the second place noted it and said to me when the guy went to the restroom, "Honey, dump him! He doesn't pay. Good riddance!" But my sister thinks that is harsh, and maybe he was just unsure if it was a real date. I know a lot of guys aren't sure what to do anymore. What do you think? I really liked him, and he wants to go out again. Should I take the bartender's cue and dump him for being cheap, or do I give it another chance? -- NOT TRYING TO “WINE”

DEAR NOT TRYING TO “WINE”: Dating is rough. I don't care what anyone says, there are no rules anymore as to who is supposed to do what. So, in this case, here's how I would play it. It seems as though he likes you because you went to a few places together. But maybe he wasn't sure if you thought that this was a "date" because you met online, and maybe he wasn't sure if you wanted it to be a date. Because he is young, he may be less confident in himself and afraid of turning you off by taking the reins. I would give it another chance. He may have not wanted to insult you, either, thinking that you wouldn't want him to buy you a drink. 

It's stupid to play games with each other. Make it clear to him that you want to go out on a date. D-A-T-E. With food. And adult beverages and good conversation and no expectation of sex right after. Get to know each other a little bit before jumping into bed and see how it goes. (And if he picks up the check, great! If he asks to split it with you, gladly do it, but then take note that maybe this isn't a date in his mind, and how many non-dates do you want to have?) 

As a side note: I have always found that if a guy was into me, or even just a gentleman, he insisted on paying for our dinner. Down the road, if we kept dating, I would then offer to pay, and usually we would take turns. You want a partner that wants to dote on you but also treats you with respect and knows the definition of reciprocity -- in all things. (But that's for another column.)

Natalie's Networking Tip of the Week: Speaking of reciprocity, remember that networking is a two-way street. If someone continually cancels on you or doesn't return your messages and phone calls, remind yourself that there are plenty of people to work with and learn from and move on. Plus, why would you want to take your cues from someone who doesn't show proper manners or decency when making plans?

Please send your relationship and lifestyle questions to or tweet them to @NBSeen. You can also send postal letters to Natalie Bencivenga, 358 North Shore Drive, Pittsburgh, PA 15212

(This column was originally published by the Pittsburgh Post-Gazette.)