Afternoon, hot boys of ManPlay! I hope you all had a relaxing and fun weekend. I got some great letters today from many of you telling me about the great dates you’d been on with men from ManPlay over the weekend. You know I love to hear about all your adventures in gay dating, so keep them coming! One letter I got addresses an issue that I’m constantly asked about. When on a first (or second or third) date, who should pay?!

Now I think we can all agree it’s an antiquated notion to assume that on a first date for a straight couple that the man automatically pays, but when I talk to some of my straight girlfriends, the majority of them seem to expect just that to happen. When I posed the question of who they think should pay on a same sex date, most of them seemed stumped. As with anything that concerns gay dating, there is bound to be a wide variety of answers to this question. In my experience I think it comes down to who has been asked out on the date. This can be tricky when it comes to online dating since it’s possible you’ll be chatting online for ages and discussing the idea of going out together before anyone actually comes up with any solid plans. In this case, it can be hard to decipher who was the one that did the official ‘asking out’ and nothing could be more uncomfortable than having a discussion when the bill comes about who should be paying.

While times are tough for most people in this economy, it certainly doesn’t start a potential relationship out on solid ground by arguing about who should be paying the bill. There are a lot of advocates for splitting the bill when it comes to dates early on and I can certainly see the appeal. It cuts down on any possible irritations and seems an all-around fair method, but there are a couple of reasons why I prefer for someone to pay. First of all, no matter what people might say, it is nice to feel like you are being treated well and have someone pick up the bill. Secondly, I think it’s a smart thing to do for the other person will hopefully feel like he will treat the next time, therefore setting up a tentative plan for a second date. That is, of course, only an asset if the date is going well. The last thing I would want is for the payment time to be awkward, so I am usually inclined to reach for it if my date doesn’t seem like he’s in any hurry to, even if I felt he was the person behind the date. While I will do this frequently, it does not start the potential relationship off on a good note as far as I’m concerned.

If you pick up the tap because you are pretty sure your date is not about to reach for it or you’ll end up haggling over the cost of each individual item that was ordered you might feel like you are being put upon from the get-go, and that is no way to start a relationship that could last even long enough to make it to a third date! Money is a tricky issue no matter how you look at it, but it really doesn’t have to be that complicated. If things are going well and you are comfortable with picking up the bill and think that it would be a nice move on your part, then I say you should go for it. The worst case scenario is that you were kind and paid for someone else to have dinner with you that night. It can be awkward if during the course of your evening you get the impression that there is definitely a pay gap between both of your salaries and yet you are the one who seems to be making less but is picking up the tab at the end of the night. Who hasn’t been in that situation? It can make things worse but being like “Oh, I guess I can pay for this…” so sometimes it’s just best to get out of the situation as fast you can. The shame about that is you don’t know if there were a lot of other redeeming qualities about your date or if he was just nervous or… That’s the thing about first dates. You sometimes have to get through a bad one to see what the person is really like the next one. Sometimes the first impression is totally accurate and other times it can be completely different the next time you meet up. Deciding on who pays for a date can be just one aspect that may make you feel like a date has gone well or hasn’t, but it’s one that can be maneuvered painlessly with minimal effort.

What do you think, men of ManPlay? Do you have any hard and fast rules for who should be paying when you’re on a date? Do you find it to be one of the most uncomfortable parts of a first date? Let me know and then be sure to discuss it with others in the chat rooms of ManPlay!

John xo

Categories: Gay Dating John