I found your substack after your most recent appearance on the Champagne Sharks podcast and I just wanted to say I appreciate what you write about so much. I’m a 27 year old straight dude struggling with dating in a big city and your writing makes me feel not crazy and not alone. I’ve accepted women and queer men don’t care all that much about men’s dating woes, but it’s always surprised me how many straight men performatively “don’t care” either. Thank you for caring and having compassion about it.
It’s one topic among many, but it’s the one that resonated with me the most because of your honesty about it. If there are other straight male substack writers doing the same thing I would be interested in more, I’m new to this app. It’s very lonely to not see anyone else talk about these things and it makes it hard not to turn to self loathing. I think men being more open about this stuff will help heal us all.
You would probably enjoy Thomas Brown’s substack. I don’t know how to link it but it’s just called “Thomas’s Newsletter.” He writes about his experiences using dating apps in NYC and when traveling.
to actually comment on the topic of the article: I go into every date assuming I’m gonna pay for everything, and view it as a large green flag when a woman even brings up the topic (or god forbid offers to split). I also don’t choose very expensive venues and find it a red flag if she has a problem with it. I don’t have a college degree and make an average salary, I feel no need to cosplay as above my means.
My twenties were brutal man, I definitely get it. Hang in there and stay true to yourself even when it’s tough. I spent a lot of years running away from me but when I came back to exploring my true, authentic self it really paid off in the long run.
I had about five years of my life when I was living off book advances too large to ever come again (my first book sold for $100,000 and my last book sold for $9,000). It was kinda great. How many people just get to do nothing for five years? Of course I never had to pay the piper--I'm 37 years old now and own a home and send my kid to private school. But it seems like Gould has a reasonable middle-class lifestyle these days too. Even F. Scott had good years and bad years--when he was churning out screen plays for money, I bet he wished he'd banked a few of those $2000 Saturday Evening Post paychecks (equivalent to thirty thousand dollars today!) But c'est la vie. What's the fun of being a writer if you've gotta treat it like an ordinary job.
When I was a man, I always paid for dinner, because I knew some women expected you to. Same as how I tip a bartender but not a hot-dog vendor: it's all just social convention.
I’d usually say something like, “if you don’t mind, I’d like to pay for dinner/etc”. It’s a good way to take the pressure off of both parties and makes the other person feel appreciated in my experience.
Then if she says thanks and that she'll get the next round of drinks or something, it's great because then you know she's not only thoughtful, but also having a good time.
Ah, you're forgetting the best rationale for figuring out how to split the check: one person only having a credit card and the other only having twenties. Happened to me the last time I went to a restaurant with a guy :P
Now, when I'm just getting dinner with a friend, quite often the paycheck comes down to "who makes more money" - I once offered to split a check with a friend when we went out, and she laughed at me. "Q, I literally work on Wall Street. I'm covering you." This is all fine and dandy when you're pals with no romantic desires, of course, but I can see why you'd want to not use that metric on a m/f date: it requires you to immediately confront the wealth gap between you and a prospective partner, and that's the kind of thing that destroys relationships (particularly if the guy earns more).
"Is it so hard to just agree that in most cases, men should pay on the first date because it makes women feel good? In most cases, the man will do the asking and will get to plan the details of the first date, so he can set his budget. I remember once seeing a TikTok about a guy who took a first date out to Carbone’s in NYC for a very expensive dinner, after which she didn’t agree to a second date. Many accused her of using him for an extravagant meal, but he chose the place! At least I’m assuming that. If he let her bully him into going to Carbone’s, he’s got other issues to work on."
It always seem to me, who was never a casual dater, that whoever does the asking should do the paying, to be pithy. And most of the time it is men doing the asking, they should do the paying. And without expectations, to be clear. You are going out with someone because you find them interesting in some way, not due to the thought of something else happening. That said, I do know men who have gotten on some track via dating apps that leads to women who find them to be just meal tickets, which is sad, but might say more about the man than the woman.
I've gone on many first dates via apps and I've never once had the free meal issue. Maybe I just give off cheap/poor vibes and instantly repel that type of woman.
I found your substack after your most recent appearance on the Champagne Sharks podcast and I just wanted to say I appreciate what you write about so much. I’m a 27 year old straight dude struggling with dating in a big city and your writing makes me feel not crazy and not alone. I’ve accepted women and queer men don’t care all that much about men’s dating woes, but it’s always surprised me how many straight men performatively “don’t care” either. Thank you for caring and having compassion about it.
Oh cool, the episode with Jessa Crispin? Hope you enjoyed that one!
Do I really write that much about dating, haha?
It’s one topic among many, but it’s the one that resonated with me the most because of your honesty about it. If there are other straight male substack writers doing the same thing I would be interested in more, I’m new to this app. It’s very lonely to not see anyone else talk about these things and it makes it hard not to turn to self loathing. I think men being more open about this stuff will help heal us all.
You would probably enjoy Thomas Brown’s substack. I don’t know how to link it but it’s just called “Thomas’s Newsletter.” He writes about his experiences using dating apps in NYC and when traveling.
to actually comment on the topic of the article: I go into every date assuming I’m gonna pay for everything, and view it as a large green flag when a woman even brings up the topic (or god forbid offers to split). I also don’t choose very expensive venues and find it a red flag if she has a problem with it. I don’t have a college degree and make an average salary, I feel no need to cosplay as above my means.
My twenties were brutal man, I definitely get it. Hang in there and stay true to yourself even when it’s tough. I spent a lot of years running away from me but when I came back to exploring my true, authentic self it really paid off in the long run.
I had about five years of my life when I was living off book advances too large to ever come again (my first book sold for $100,000 and my last book sold for $9,000). It was kinda great. How many people just get to do nothing for five years? Of course I never had to pay the piper--I'm 37 years old now and own a home and send my kid to private school. But it seems like Gould has a reasonable middle-class lifestyle these days too. Even F. Scott had good years and bad years--when he was churning out screen plays for money, I bet he wished he'd banked a few of those $2000 Saturday Evening Post paychecks (equivalent to thirty thousand dollars today!) But c'est la vie. What's the fun of being a writer if you've gotta treat it like an ordinary job.
When I was a man, I always paid for dinner, because I knew some women expected you to. Same as how I tip a bartender but not a hot-dog vendor: it's all just social convention.
Damn, $100k was quite the advance. A much-delayed congrats!
I’d usually say something like, “if you don’t mind, I’d like to pay for dinner/etc”. It’s a good way to take the pressure off of both parties and makes the other person feel appreciated in my experience.
Then if she says thanks and that she'll get the next round of drinks or something, it's great because then you know she's not only thoughtful, but also having a good time.
Ah, you're forgetting the best rationale for figuring out how to split the check: one person only having a credit card and the other only having twenties. Happened to me the last time I went to a restaurant with a guy :P
Now, when I'm just getting dinner with a friend, quite often the paycheck comes down to "who makes more money" - I once offered to split a check with a friend when we went out, and she laughed at me. "Q, I literally work on Wall Street. I'm covering you." This is all fine and dandy when you're pals with no romantic desires, of course, but I can see why you'd want to not use that metric on a m/f date: it requires you to immediately confront the wealth gap between you and a prospective partner, and that's the kind of thing that destroys relationships (particularly if the guy earns more).
"Is it so hard to just agree that in most cases, men should pay on the first date because it makes women feel good? In most cases, the man will do the asking and will get to plan the details of the first date, so he can set his budget. I remember once seeing a TikTok about a guy who took a first date out to Carbone’s in NYC for a very expensive dinner, after which she didn’t agree to a second date. Many accused her of using him for an extravagant meal, but he chose the place! At least I’m assuming that. If he let her bully him into going to Carbone’s, he’s got other issues to work on."
It always seem to me, who was never a casual dater, that whoever does the asking should do the paying, to be pithy. And most of the time it is men doing the asking, they should do the paying. And without expectations, to be clear. You are going out with someone because you find them interesting in some way, not due to the thought of something else happening. That said, I do know men who have gotten on some track via dating apps that leads to women who find them to be just meal tickets, which is sad, but might say more about the man than the woman.
I've gone on many first dates via apps and I've never once had the free meal issue. Maybe I just give off cheap/poor vibes and instantly repel that type of woman.