Etiquette of paying on dates

[MacadamiaNut]

OP, I didn't mean to imply you were in fact looking for problems.  I'm sorry about the way that sounded - I should have edited better!  I was saying it more as one of those quotable phrases and more to provide another perspective to the gender role comments.  i.e., if everything feels right, it may not be necessary to jump to any negative conclusions about his thoughts on "gender roles".

He smiled when you offered to pay which is awesome!  Good for you!   

[blueberrypancakes]

Ahhh see this is what happens when things are typed not spoken.  I didn't think you were implying that, I should've added a smiley or something. 

I'm definitely not seeing it as a gender role thing.  I just see it as him being a super nice guy and I just don't want to take advantage of it or anything, hence me grabbing the bill once in awhile.   

[MacadamiaNut]

No worries.     I agree.  As long as you don't sit around doing absolutely nothing to show kindness in return it should be fine!  And it looks like you definitely want to do nice things for him as well.  I find guys like this are happy with any gesture.  i.e. if he buys you a $100 dinner and you treat him to an ice cream cone in the park later, he's usually ecstatic - it's not about the money.  It's the gesture and thought behind it.  At least that's been my experience with these "types".  He sounds like a great guy!  All the best!

[saki]

For me, it's a turn-off if a guy insists on paying for everything.  I like to pay my own way.  I also like to be the one who gets to treat sometimes, it makes me feel good.  In particular, it's the INSISTING on paying that gets to be a turn-off for me.  It reminds me of this one guy a few years ago, we had a date at his place which was on a slightly dodgy road, he said "let me call you a cab", I said "no, that's fine, I'm happy to walk", he's all "no, you have to take a cab" I'm like "I spent two years living around here, I'm quite comfortable walking" and then he actually starts to call a cab.  I just walked out.

Or, in short, I think it's a good sign that the OP's date has now started letting her pay!  Insisting on paying when your date specifically says that they'd like to do so is not polite.

[Allyson]

For me it would depend on financial situations--if someone made a lot more than I did, i would be way more likely to be OK with it. Whereas if the ONLY reason he would be paying is that he's 'the guy', that wouldn't be appealing to me.

I find it a little uncomfortable that often women are expected to like this behaviour and accept it because he's 'being a gentleman'. Whereas in a reversed situation, with a couple making similar amounts of money, if it was the woman who wanted to pay for everything and kept saying "it's how I show I love you, it's how I was raised" I think people wouldn't be so quick to tell the boyfriend he should just shut up and be grateful.

[Chivewarrior]

For me, it's a turn-off if a guy insists on paying for everything.  I like to pay my own way.  I also like to be the one who gets to treat sometimes, it makes me feel good.  In particular, it's the INSISTING on paying that gets to be a turn-off for me.  It reminds me of this one guy a few years ago, we had a date at his place which was on a slightly dodgy road, he said "let me call you a cab", I said "no, that's fine, I'm happy to walk", he's all "no, you have to take a cab" I'm like "I spent two years living around here, I'm quite comfortable walking" and then he actually starts to call a cab.  I just walked out.

Or, in short, I think it's a good sign that the OP's date has now started letting her pay!  Insisting on paying when your date specifically says that they'd like to do so is not polite.

Well that guy was actually being controlling. If you'd been taking a cab anyway I don't think it would have been rude to insist on paying for it; it was rude to insist that you take a cab.

[saki]

For me it would depend on financial situations--if someone made a lot more than I did, i would be way more likely to be OK with it. Whereas if the ONLY reason he would be paying is that he's 'the guy', that wouldn't be appealing to me.

I find it a little uncomfortable that often women are expected to like this behaviour and accept it because he's 'being a gentleman'. Whereas in a reversed situation, with a couple making similar amounts of money, if it was the woman who wanted to pay for everything and kept saying "it's how I show I love you, it's how I was raised" I think people wouldn't be so quick to tell the boyfriend he should just shut up and be grateful.

I agree.  Apart from anything else, women also like to show their appreciation/love through treating people and why should they not be allowed to do that because of their gender? 

I think insisting on paying when the other person has said that they aren't comfortable with that is not nice or polite.