After How Many Dates Should I Offer To Pay For Dinner? Ask A Pro

Email Head Pro your questions about life, love and coerced smooches to

Dear Head Pro,

So I have this same internal conflict every time I start dating a guy and my besties are all over the place with their advice, but I have faith you'll be able to settle this for me. Whenever a guy asks me out on a first date, I always let him pay because like, he's the one who asked me out. But if I see him again, should I offer to split the bill? Is the second date too soon to offer to split? Do you like when a girl offers to split the bill even if you're the one who asked her to dinner? Is splitting the bill something that only like established couples do? Guys usually decline my offer to pay, probably because they know I'm currently living on student loans/ broke af. I just feel like I always get awkward when the check comes and there's got to be an easy answer to this.

Also I just thought you should know that I love everything you write on here and if you ever asked me to dinner with you I would totally go splitsies.


Poor grad student betch

Dear Poor Grad Student,

Hey, a thoughtful question! The standard, “etiquette guide” answer is that, yes, the person who does the asking does the paying. That’s a fine metric to follow, especially since before the two of you become anything even approaching a “thing,” he’s likely to be doing all of the asking. If that’s the case, then he shouldn’t be asking you out on dates he can’t afford to cover. If you feel bad and want to mix it up, don’t be afraid to throw out a date idea yourself, or augment his with your own. Something like “Drinks on thursday sound great, but I’d also really like to see this movie. How about the 4:00 showing, my treat?” Once you’re in a real relationship, I find all of that shit goes out the window and the two of you live more or less according to who can afford what.

The other side of that coin is yes, guys ABSOLUTELY appreciate you at least making the gesture to pick up the tab or go dutch. It’s kind of sexy in a way, in the sense that it show’s you’re considerate and aren’t operating in “waiting for my prince” mode full-time. Even when we fully expect and plan to pay for the evening, seeing a woman just stare at you expectantly when the check comes leaves a bad taste in your mouth. It would be like even if you had planned to fuck a guy that night, but then he turned paying the check into some big to-do and acted like you owed him something. It vaguely smacks of exploitation, and doesn’t make you feel good. So yes, it’s always nice when the girl offers to go halfsies.

If we went to dinner, I’d make YOU pay the bill,,

Head Pro

Dear headPro,

As a freshman in college I have been struggling with figuring out if a guy likes me BUT, there is one in particular that confuses me more than others. We met the first weekend of college at a dance and we hungout the whole time, danced, he bought me drinks and had a good time, he got my number and texted me later that night but the next morning he stopped replying. Being a girl I wanted to wait for him to text me first but it never happened. Since then we had hung out 3 more times at different parties and dances, again dancing and flirting and hanging out the whole time. He has texted me maybe once or twice within a 4 month span so I gave up and moved on to other guys completely forgetting about him… Until this past weekend.

We saw each other at another bar where again we danced and he bought me drinks and hung-out the whole time…But this time was different he went home with me at the end of the night, we kissed and cuddled but he abruptly left at 3AM but gave me a goodnight kiss… See where im going?? Its confusing right? But it has been 4 days since and still no text. Im especially confused because he willingly came to my room at the end of the night, but i had to coarce (sic) him to kiss me by saying “why have you been flirting all night but haven't made a move?” so he kissed me and I said “I don't want to make you kiss me, you don't have to be here” and he said “I wouldn't kiss you if i didn't like you” keep in mind I was hammered while he maybe had a couple drinks…So i woke up the next morning and he had left his phone in my room i thought i was being nice so i put it in his PO box but when i told him he seemed disappointed by messaging me “oh how thoughtful of you” in a condescending tone… I do know only a year ago he got his heart broken by a very long term relationship, but still I can't tell what I did wrong, he always acts like he likes me so much but I have to make all of the first moves! Please help me decipher this confusing man.

Thank you,

A very confused girl

Dear Confused,

Where is your college located that you have dances, the 1950s? This is actually not that confusing, really – this is a rare time when “he’s just not that into you” is really about all you need to tell you what’s going on. Since you’re young, I’ll break it down for you:

“Willingly going to your room” after a night out is not a good metric for determining whether or not a guy likes you. If it were, every girl would be the most popular girl on campus. It’s unwise to take his admission of liking you and not being coerced into kissing you at face value when you did, in fact, coerce (sorry, coarse) him into kissing you. You don’t have to passive-aggressively goad people who like you into smooches.

You’ll drive yourself crazy trying to infer tone and/or read between the lines from IMs. Putting his phone in his PO box was actually thoughtful of you; he probably meant it that way. Although, you’d have given yourself another opportunity for smooch coercion if you’d just left it in your room. Rookie mistake.

Where are you getting the idea that he “always acts like he likes you?” The fact that it’s nearly March and he hasn’t texted you since August? That you’ve been in the same place at the same time on a handful of occasions? IS IT THE COERCED SMOOCHING?

You haven’t done anything wrong, so relax. There’s just nothing between you and this guy beyond maybe a passing interest on his part. I get that the buying drinks and going to your room may lead you to believe otherwise, but I think, honestly, he’s just being polite. Some guys see it as their “responsibility” [wanking motion] to pay for girls’s drinks, and when a drunk girl at 2 AM wants you to kiss her, you kiss her, dammit. Other than that, I’m sorry. He’s just not that into you.

Kisses of my own free will,

Head Pro

Email Head Pro your questions about life, love and coerced smooches to


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