I’m Always Picking Up the Check, and I Hate It!

Hey T,

Do you think it’s fair that this guy I’ve been seeing always expects me to pick up the check when we go out?  We’ve only been dating for about 3 weeks, and no matter where we go, he expects me to pay for both of us.  I’m getting tired of it.  He never offers to pay.  Don’t get me wrong, I have the funds to pay, I just don’t feel like it should be on me to do so every time.  Especially when he is a grown man.  What would you do in this situation?


No Moocher

Dear No Moocher,

Thanks for writing to me.  This has been a hazy area in the gay dating world for quite some time.  Since that it is the case, I’m sure everyone won’t agree on my take with this issue.  Which is fine.  However, I think my perspective is a fair one.

For starters, when two people are preparing to go on a date, I think the inviter should go with the anticipation of paying for both him and the invitee.  For example, if you ask a guy out to Maggiano’s for dinner followed up with a movie, you should anticipate you will be paying for his food and ticket along with yours.  You planned the date knowing the costs associated with the evening, and should be ready to pay.  Short and simple.

With that said, it shows me a lot about the potential for a real relationship with a person if he doesn’t at least volunteer to pay for his portion of the date.  Or if after a nice time out, he doesn’t recommend going on another date in the near future where he pays.  Look, I don’t “keep” men, nor do I want to be “kept.”  I’m all for a relationship being both a friendship and a partnership.  That means sometimes I hold you down for the evening, and sometimes you hold me down.  And heck, sometimes we are together and we hold ourselves down. LOL!

Based on the letter, it sounds like you don’t want to fund a man any more than I do.  So don’t.  I’m not sure if you have been the only one planning when you and him go out, but if that’s the case, stop it! Let him make plans for the next date.  Besides, if you two only go out when you ask and he never pays, that could potentially signal a bigger problem here.  That could signify that while he may like you, he is more into what you pay for.  But let’s not jump the gun.  Just keep that in mind going forward.

Suggestions going forward.

  1. Again, don’t schedule another date. See if he will plan something. If he does ask you out, make sure when the bill comes, you fight the urge to grab it.  Leave it on the dinner table, and wait for him to extend his arm to get it.  If some time goes by, and it gets awkward because he hasn’t attempted to whip out his wallet, give him enough cash to cover your portion of the check only, and abort this “situationship.”  So I recommend driving separate cars, or at least making sure you have an Uber on standby.


  1. I didn’t talk about it, but some folks think the top should always be designated to pay for him and the bottom. Since you sound tired of paying for people, please don’t buy into this philosophy.

As always nothing but love,


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