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Dating Etiquette

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How do the gays decide who pays? Is it always the bear or whatever?
In my experience, whoever extends the invitation always pays for everything. If I offer to take a guy out on a date, then I just pick up all the tabs, I'd be thoroughly embarrassed to act like I had to save my money for tomorrow night's twink. That also ties into the fact that I've never had to go out on a date to get laid with a guy, generally those encounters take place without any sort of formal arrangements to hang out.

When I take someone out on a date, it's because I want to express a sincere interest in getting to know him better, not because I want someone to help subsidize my entertainment for the evening because I'm too lazy to get a job.
 
In my experience, whoever extends the invitation always pays for everything. If I offer to take a guy out on a date, then I just pick up all the tabs, I'd be thoroughly embarrassed to act like I had to save my money for tomorrow night's twink. That also ties into the fact that I've never had to go out on a date to get laid with a guy, generally those encounters take place without any sort of formal arrangements to hang out.

When I take someone out on a date, it's because I want to express a sincere interest in getting to know him better, not because I want someone to help subsidize my entertainment for the evening because I'm too lazy to get a job.

Not sure why you keep bringing up the job issue, because that has nothing to do with the topic at hand. Unfortunately, most girls don't put out as easy as the gays do in your informal manner.
 
I bring it up because I think it's disingenuous to be claiming that you want your dates to pick up some of the entertainment expenses out of "principle" when the real reason is that you have to carefully watch your expenses because you're not working. Do you ever just tell these girls, "Hey, I'm not working right now, so you need to know up-front if we're going out that I'm only able to buy a few rounds or so." Or do you withhold that information because you think it would negatively impact your chances of getting laid or even going on the date in the first place?
 
I bring it up because I think it's disingenuous to be claiming that you want your dates to pick up some of the entertainment expenses out of "principle" when the real reason is that you have to carefully watch your expenses because you're not working. Do you ever just tell these girls, "Hey, I'm not working right now, so you need to know up-front if we're going out that I'm only able to buy a few rounds or so." Or do you withhold that information because you think it would negatively impact your chances of getting laid or even going on the date in the first place?

We met at an online dating site, where we submitted the options: Looking to meet new friends; Short term dating; Long term dating. So it should be assumed the 'first date' is possibly just two people meeting up for a possible 'friendship'. Why should I be liable for all of the 'entertainment expenses'? Before we met, it was known I am unemployed because in the primary online discussion I tell them, "I literally just moved here last week". I am still claiming it is out of 'principle'. If my expenses were unlimited, I still don't think I should have to cover all the entertainment expenses of the 'date'.
 
So by clicking multiple check-boxes on a dating web site, you're implicitly reserving the right to decide on-the-fly whether these initial encounters are just "friendships" where everybody goes Dutch or "possible hook-ups" where you're okay dropping a little more cash? Would that mean that your date is also afforded the same luxury? What if her reticence to offer to pay was motivated by a decision to consider you "just a friend" and not worthy of dropping more cash on? Perhaps she was simply exercising the rights you reserved to yourself.

There's a real simple solution to this conundrum. The person who extends the invitation to hang out, no matter how casually it's made, is on the hook to pay for the group's expenditures. This holds true regardless of race, gender, religion or sexual orientation. If someone else steps up freely to help with the bills, that should be a pleasant surprise and not an expectation. This has the benefit of making sure that you only extend invitations to spend time together to people who are really worth it, and removing any awkward moments related to who pays the check. If you want to hang out but can't afford to extend an invitation, don't then accept one as a form of charity; make sure you spend at least as much time filling your own wallet as you do emptying someone else's.
 
So by clicking multiple check-boxes on a dating web site, you're implicitly reserving the right to decide on-the-fly whether these initial encounters are just "friendships" where everybody goes Dutch or "possible hook-ups" where you're okay dropping a little more cash? Would that mean that your date is also afforded the same luxury? What if her reticence to offer to pay was motivated by a decision to consider you "just a friend" and not worthy of dropping more cash on? Perhaps she was simply exercising the rights you reserved to yourself.

There's a real simple solution to this conundrum. The person who extends the invitation to hang out, no matter how casually it's made, is on the hook to pay for the group's expenditures. This holds true regardless of race, gender, religion or sexual orientation. If someone else steps up freely to help with the bills, that should be a pleasant surprise and not an expectation. This has the benefit of making sure that you only extend invitations to spend time together to people who are really worth it, and removing any awkward moments related to who pays the check. If you want to hang out but can't afford to extend an invitation, don't then accept one as a form of charity; make sure you spend at least as much time filling your own wallet as you do emptying someone else's.

I suppose this makes sense.

Is it ever acceptable to only purchase a drink for myself in the middle of the 'hang out'?