He says he's old-fashioned, but keeps letting me set up dates, and pay

Anonymous
Been out with this guy twice now, with a third date scheduled for tomorrow. We're both in our mid-30s, met online. Both university-educated and have good jobs.

His profile said he was a bit old-fashioned, and so I'm a bit surprised at some of his choices. For our first date, he asked me out, and chose the restaurant. It's worth noting that I had suggested just drinks, but he wanted dinner so we could get to know each other better. At the end of the date, when the bill came, I pulled out my credit card, and he pulled out his, and we split the bill. I'm cool with that, but would pay for someone's dinner if I was the one who said we should have said dinner, instead of just drinks like they suggested.

Second date, he asks, but suggests that I pick the place. He then insists I pick the wine, and the appetizers we share. When the bill comes, I'm in the bathroom. When it's time to leave, he gets up from the table and just leaves the little bill-container-envelope on the table. I think maybe he paid while I was in the bathroom, but don't want to assume anything, so I grab it and follow him. At this point he's like, right, we should pay at the bar. So I put my card into the little holder thing, he puts his on top of mine, and gives the envelope thingee to the bartender. Apparently the bartender put the whole total on his card, because he asks bartender "aren't you going to split this?" Bartender then splits it, and we each pay half.

For our date tomorrow night, again he suggested I pick the restaurant, so I have. I guess I'm just confused. I'm cool with splitting things (wouldn't keep agreeing to dates if I wasn't) and I have plenty of restaurants I like that I can suggest, but it seems odd that he's pretty insistent about both since he specifically mentioned he's old-fashioned. He does seem old-fashioned, in that he told a story about wanting to make sure his sister's fiance was able to financially take care of a family. It's worth noting that just on these two dates, we've established that he's a pickier eater than I am, so having me choose repeatedly doesn't necessarily make sense. He definitely seems interested, in that he contacts me daily, wanted to see each other twice this weekend, etc. All I can figure is that maybe he's letting me pick the restaurants because he doesn't want to suggest anything himself that might be more than I wanted to spend, since I'm paying for myself?

Also might be worth noting that he hasn't asked for my phone number, or given me his, yet. I've never gone on more than one date with someone from online before that happened. We're still just messaging on the site.

So, thoughts? Why the insistence on me choosing (from the locations to the wine to the food)? Why the deliberate bill-splitting, if he's old-fashioned? Is he just not that into me? I fully expect a number of posters to flame me for even mentioning money and say I'm a gold-digger, but other than not posting this, I can't control it.
Anonymous
If you expect him to pay (which it sounds like you do) then don't reach for the bill. Let him reach for it.

If you are "cool" with splitting, then be cool.

Someone can be "a bit old-fashioned" and still feel that in the very preliminary stages of on-line dating, they should not have to foot the bill because that's not really a relationship and they shouldn't have to pay all the freight. Once that person is in a solid relationship, then they would pick up the tab, every time.

The fact that he hasn't asked or your phone number and lets you take the lead on restaurant choice and pay all the time indicates to me that he is ambivalent. I would stop messaging him and lay back -- way, way back.
Anonymous
I think the phone number thing is strange. The bill payment part is always awkward, I think. I personally would expect the guy to pay if he invited me (esp. for the first date), but I'm old-fashioned (more so than your date, it seems).

I believe he's trying to be egalitarian by suggesting that you choose the restaurant/food & think perhaps he's trying not to be as picky as he knows he actually can be.

Do you like this guy?
Anonymous
Anonymous wrote:If you expect him to pay (which it sounds like you do) then don't reach for the bill. Let him reach for it.

If you are "cool" with splitting, then be cool.

Someone can be "a bit old-fashioned" and still feel that in the very preliminary stages of on-line dating, they should not have to foot the bill because that's not really a relationship and they shouldn't have to pay all the freight. Once that person is in a solid relationship, then they would pick up the tab, every time.

The fact that he hasn't asked or your phone number and lets you take the lead on restaurant choice and pay all the time indicates to me that he is ambivalent. I would stop messaging him and lay back -- way, way back.


It's not so much that I expect him to pay, but that I wonder what it says that he makes a point of saying he's old fashioned, and then doesn't pay, if that makes sense. If he hadn't pointed out out, that he was old-fashioned, I wouldn't be surprised. Like you indicated, I am wondering if he is old-fashioned, and is still letting me make the choices, and pay, if he just isn't that interested, in spite of how much he contacts me.
Anonymous
I think he has a different idea of old-fashioned than you do, that's all. He's not connecting it to paying the bill, etc.
My personal feeling is that whomever does the inviting, pays - but I guess since the guy is often the one doing the inviting, that makes me old-fashioned, too. Regardless, I don't think any of this reflects how into you he is...he keeps inviting you out and wanting to see you, right? How is your connection otherwise?
Anonymous
Ran into this before with a guy from an online site.

I am old fashioned. If I am paying, it's not a date, it's just hanging out with a friend. So after a couple months of going out and splitting the bill (all told a couple months meant we had been out maybe 4 times - hard to coordinate schedules) I mentioned going out on a date with someone from the same site and he got all huffy and asked how I could do that. I told him that I didn't consider us to be dating. He had also said he was "old fashioned" but no, he was just really cheap.
Anonymous
The guy is cheap. Call me old-fashioned, but if he's trying to court you, he should be supping for these dinners...
Anonymous
Anonymous wrote:The guy is cheap. Call me old-fashioned, but if he's trying to court you, he should be supping for these dinners...


+100
Anonymous
Anonymous wrote:I think he has a different idea of old-fashioned than you do, that's all. He's not connecting it to paying the bill, etc.
My personal feeling is that whomever does the inviting, pays - but I guess since the guy is often the one doing the inviting, that makes me old-fashioned, too. Regardless, I don't think any of this reflects how into you he is...he keeps inviting you out and wanting to see you, right? How is your connection otherwise?


Agree with pp. Different people have different ideas about what it means to be old fashioned. The phone thing is strange, though. He may be contacting you frequently, but he doesn't feel a strong connection to you. That may develop, but he's definitely not there yet.
Anonymous
He sounds married to me.

He is contacting you online because he doesn't want you to be able to call/text him. He is making you pick the restaurant because he doesn't live in your neighborhood, and has been out of the dating scene for awhile and doesn't know the places to go on dates anymore. He is splitting the bill so that the charge is reasonable for one person.

Are you sleeping with him?
Anonymous
Have anyone's genitals gotten wet yet in this relationship?
Anonymous
I don't think the messaging thing is that big of a deal, he's probably just uses to contacting you that way and it works well, but I would definitely ask him for his phone number, even with a white lie about how your data plan on your phone or poor internet connection in your house somewhere if you'rw uncomfortable just asking. If he hesitates, then yes that's a red flag

With the bill-split thing, online dating can be expensive before you find "the right one" if you are paying for 2 meals all the time. Imagine a scenario where someone had bad first dates, lack of interest after a couple dates, repeatedly, and was spending $500-1000/ month on dinners and drinks. At $100/meal ( for 2), 4-6 dates a month starts to add up.

Maybe I'm in the minority, but that would be a lot of money month after month.
He's obviously really into you, if you like him I wouldn't stop dating him over this
Anonymous
Perhaps next time he refers to himself as old-fashioned, ask him what he means by that. There's nothing wrong with wanting to split the check, but it is odd for someone so insistent on his old-fashionedness. I'd want to know exactly what that encompasses to make sure it isn't something that will be problematic down the road (e.g., he's only old-fashioned when it benefits him, so if you move in together or get married at some point, he'll expect you to manage the household cooking, cleaning, etc., but will still expect you to also work).
Anonymous
1) ask for phone number. Be direct 3rd date, time to start contacting directly.

2) ask what old fashioned means? Does it mean wait till marriage for sex? Does it mean "I expect the woman to do the cooking, cleaning and child care while I work and play golf?" etc. so many different iterations of this.

3) I always preferred splitting or alternating the bill when I was dating because I never felt that I "owed" any man anything, and if I decided I wasn't into someone, at least they didn't feel like they were used. That being said, most men who were really into me at least tried to pay. Once dating is established, I prefer alternating, being taken out or taking someone out, but not splitting (seems so...miserly).

4) if you and he are both gainfully employed, there's no reason why you shouldn't pay, particularly in the early stages in the relationship for all sorts of reasons. (If we women want to be paid equally in the workplace, we should expect equality in other ways). That being said, I would pay more attention to other things--how he treats you, other people, whether he can move to the next stage in the relationship, etc. If you keep dating you will be able to figure out whether he is, in fact, 'cheap' which is different (poor tipper, unable to ever enjoy the pleasure of treating someone, refusal to spend within means), egalitarian, hesitant, or just economical


Anonymous
8:48, do that. Great advice
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