Q: Your boyfriend offers to buy you dinner and one of your girlfriends is there. Is it rude for him not to pay for her meal, too?
A: It depends on how everyone came together.
If you and your girlfriend planned to go out and your boyfriend joined in, it would be awkward for him to pay for your meal but not hers. But if you and your man were the ones looking forward to eating out and your girlfriend was the late addition, expecting him to pay for her would be assuming too much.
If the three of you all chose a time and place together, then this is a group outing and your boyfriend should not feel obligated to pay for your friend; people usually pay for themselves in group outings. Of course, if your boyfriend invited you and your friend out, then he would be the host and, as such, would be expected to pay for everyone.
ELAINE SWANN, lifestyle and etiquette expert
A: The expectation of your boyfriend paying easily could be interpreted by him — as well as you and her — as an attempt to gauge if he cares about your friend.
He can show that he cares about her in other ways than paying for her meal. He should invest in your friend through his actions during dinner, including actively listening when she speaks. He should be genuinely interested in getting to know her, too. Putting in the time to connect with her is the best compliment he could pay her and shows much more respect and compassion than buying a meal.
Him offering to paying for your friend comes off as trying to suck up to her. It makes it seem like he needs to offer something additional for her to like him.
NICK NOTAS, dating and confidence consultant