Tuesdays with the Pretty Girls: Footing the bill – When is enough enough?

Mr. Davidson is quite smarmy, I'm told.

“How much shit do I have to pay for?” – Anonymous

I am not sure that there is a right or a wrong answer for this question. Sure, the old school way is that the guy should pay for everything, but Im not exactly completely old school.  For example, me picking up the occasional tab, movie tickets or whatever it may be is fine by me as long as I am the one offering. If you ask me to pay then I am going to assume that you are the cheap as and just looking for a sugar momma.  A sugar momma I am not but again, I am not expecting daddy warbucks either.

I don’t think most girls look at guys as walking moneybags. There is a fine line between being a gentleman and paying for the date and trying to buy the girl. Gifts are very sweet and greatly appreciated but no one is asking you to drop your entire paycheck on a present. Its the thought you put into it that really counts.  The smallest things usually mean the most if you put your heart into them, so keep that in mind.

For the first several dates, gents––all of it. No question. If she should offer, I recommend politely refusing. When, and hopefully if, your dates progress to regular and frequent status she should offer to pick up the tab on occasion. Splitting the check or letting her pay sometimes is perfectly acceptable. If she invites you out, she should offer to pay; whether you let her or not is up to you.

Paying protocol depends on where you are in your relationship. Is it the first date and I’m not feeling you? Yes, pay for me please. Is it the first date and this is going somewhere? Then I will offer to split the bill. Is this the 4th date and you’ve paid for me for the first 3 dates and this is headed toward a relationship? Then I’ll offer to pay. Is this a 6 month relationship, neither of us cook, and we always go out? I’m offering to pay probably every 3rd to 4th meal. I like a guy to pay if he can, but I’m not so high maintenance that I expect him to pay all the time. When all else fails, there’s always the Dollar Menu (which I’m a fan of) at McDonald’s.

How long do you want us to pay for our waxing, plucking, tanning, hair dying, cute panties, makeup, birth control and everything else we pay for to get ready for dates?


I’ve had the pleasure of treating one of these pretty girls to drinks and appetizers on a few occasions. I’ll color you jealous now. Don’t be afraid of the credit card, gents. It pays off.

Questions for the ladies? Submit them now.


7 responses to “Tuesdays with the Pretty Girls: Footing the bill – When is enough enough?

  1. In my relationship, I offer to pay quite often. He doesn’t usually let me, but does humor me every once in a while. Point is, if we have comparable salaries, there’s no point in letting him pay all the time.
    As most of the ladies said, if it’s still early on in your courtship, I would let him pay. If I invite him out, I will likely pay. Sounds like there’s a pretty solid consensus all around, no?

    Live Love LA

  2. In my last relationship, he paid for everything and it was sometimes difficult to get in there and give the cashier/waiter my credit card. He also always paid for my sister, one of the pretty girls above (Rebecca), for meals and movie tickets if she was with us. He’d go to the bathroom mid-meal and slip the waiter his credit card so that we wouldn’t get the chance to pay. I loved it (he’s an overall generous guy not only to me but others- a bonus quality), but the times I managed to give my credit card to the cashier first, I felt better about those times. I felt like I was able to take care of him/feed him and that feels good when you love the person. It’s all relative to how you feel about the guy and the relationship.

  3. What I do is when I invite the guy out I pay, when he invites me out he pays.

  4. Was very lucky that the last guy I went out with was generous and paid for me all the time. Most times I couldn’t get money out fast enough to even offer to pay. In return I cooked for us every 3rd or 4th meal and helped watch his apartment and trucks when he traveled overseas for 8 weeks.

  5. Nicole from Chicago fails to account for the grooming and outfitting of the guys taking her out. You are responsible for your own appearance, if you require more to make you look and feel good for a date that is your choice and your responsibility. If you need a nice die job and a new pair of Tori Burch shoes to get ready for a date, that is on you.

  6. I would argue that this economic conundrum has another angle that must be considered: age. I lived in Chicago for the time period I consider fondly my “coming of age.” Learning about girls, knowing how to treat them and in the end acknowledging, we’ll never figure it out.

    When I turned a hard working professional – at the age of 23 (grad school hurt), I dated mostly girls who were two years younger than me. I would have minded them paying on occasion, in fact, I would have welcomed it. But awkward moments aside, the girls I dated never really volunteered. Even the long term relationship I was in, in the three years I dated her she never really paid. I attribute it to younger girls who don’t have a firm path in life… yet.

    I’m a bit older and wiser now; accordingly, I date older girls who are my age. Now, the girls I date are established, have a plan for where they want to go in life, and yes, they always want to pay. I stop them. It’s surprising how a few years, a stable job and a career will change the ways girls interact financially.

  7. In my last relationship, I would always try and pay. However, a year or so in, she was pretty good about treating me to a night out every once in a while. If she would beat me to the counter or grab the check first, I tried not to put up much of a fight. My thoughts are, if there is an argument over who’s paying, and it lasts more than 10 seconds, all generosity and sincerity goes out the window. You’re basically just fighting so you can say you’re the one who picked up the bill. That said, if the lady doesn’t offer to pay, a gentleman always will.

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