Who Pays The Bill If You Are A Prospective Client?

Have you ever wondered who pays the bill if you're a prospective client? I found myself asking this very question when I made plans with a realtor I was considering hiring. It all started when I went to an open house and met a realtor named Sally. 

I was immediately drawn to Sally due to her wealth of knowledge. I'm currently very interested in building my real estate portfolio given the lag in property prices and very attractive rental yields vs. borrowing costs.

As a result, we got to talking and we agreed to have a follow up conversation during happy hour sometime in the future. Realtors are always looking for new clients. And I'm always looking to get up to date about the real estate environment. This post is not a topic of whether one should be buying property now. It's about deciding who pays the bill.

So Who Pays The Bill?

The last time I let a woman pay the bill was never, especially for an acquaintance I hardly know. In fact, even for new male acquaintances, I always pay the bill. It's just the way I grew up.

I asked the Twitter community whether I should pay or not since I am a prospective client. And I immediately got a range of responses from “don't be that guy,” to “you are sexist for even thinking about wondering whether you should pay.” 

Pretty tough responses, which leads me to believe that sharing any questions I have in public just opens oneself out for attack. I also understand why people shy away from others and keeps things to themselves.

The Reason For Conflict

The reason why I was conflicted was because I didn't want the real estate agent thinking I was being presumptuous and sexist for paying. Nor did I want her to feel she needed to reciprocate in any way. I didn't want her thinking just because I was the guy, that I should pay.

Then again, hardly any women I've been out with have ever insisted on paying. And when they do offer to pay, I can tell they are just being courteous and not entirely serious, which is something I do appreciate. I hate that moment of awkwardness when the bill comes and nobody takes initiative to grab the bill. That's called having alligator arms.

I grew up in a culture that basically requires you to fight tooth and nail to pay the bill. I've seen my parents climb over their fellow diners, fighting to take care of the cheque. And, I've seen friends pretend to go to the bathroom an hour into dinner, to actually go find the server to pay the bill without us knowing! I've even seen adults proclaim that another party is dishonoring them if they dare pay for them too!

Bring Your Own Balls

If anybody REALLY wants to pay the bill they can. Perhaps I'm just more determined than others? It's kind of like when I go out on the tennis court and my opponent who is on a 5 match losing streak and is supposed to bring balls asks, “Do you have balls?”

We're playing at a damn tennis club that sells tons of balls. So him asking whether I have balls just means he doesn't want to provide balls. But by golly, if you are going out for a drink with me, I plan on paying! 

And that's what I did with the realtor. I ended up paying the $60 bill. She didn't offer to pay, and I didn't expect her to. I was happy to pay, and she was happy to spend some time to get to know me.

Further Reading

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Readers, are men sexist for wanting to pay the bill? If you really wanted to pay the bill, do you think you could?  Should women be more aggressive in paying the bill? Is chivalry a synonym for sexist pig? Is the woman who said she is offended by my question on Twitter ever going to find a man?



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59 thoughts on “Who Pays The Bill If You Are A Prospective Client?”

  1. She should look at it as a business expense right? But I donno, maybe I have a way to make her feel like it’s not a business outing and more of a friendly drinks thing, so I ended up paying.

    Yes, a guy should make a gesture to pay imo too if it’s a date.

  2. Invest It Wisely

    So Sam are you really Japanese? I’m not sure how it is in the Japanese culture, but in the Chinese and Korean cultures the culture is similar to your own experiences: people “fighting” to pay the bill. Splitting is a Western thing and not really common to them.

    In my own view whoever invites should probably pay, and if the parties know each other well then they should probably either split or rotate…

  3. 20 and Engaged

    I’ve been with my fiance for 3 1/2 years, and we’ve taken turns with the bill. If you really calculate it, I’ve paid more than he has. Usually because I’ve made more than him during the majority of the relationship.

  4. What generation are you from? I am shocked that there are still men alive who feel that they should pay? You are a dying breed. I am a GenXer, and I have yet to meet a man under 50 years old who understands chivalry such as paying when with a woman. I fault women because they mistake chivalry for sexism. I applaud you. You must be a baby boomer.

  5. In my opinion, if it’s a date (casual or romantic) the man should pay. If it’s business, both parties should be treated equal and the party that is the vendor should be the one picking up the tab. So you just have to figure out who’s gains the most from the meeting. You with your gained knowledge or her with her potential commission from being your realtor.

    My boss is female and I have no problem with her picking up the check. After all, she has the expense account.

    You’re not sexist for asking the question, just real and intelligent.

  6. I would say that you should take care of the bill, not because you are the man, but because you are expecting her to share her knowledge of real estate. That is the benefit for her: she gives you the information that you’re looking for, and you pay for it by picking up the bill. I would give the same response if the realtor was a guy. It’s the same thing.

    1. Let’s say I am in the market for a $2 million house. A buying agent earns about 2% ie $40,000 if I purchase. Does that change things on whether or not she picks up a $40 tab?

  7. The chivalrous part of you wants to pay, but if it were a dude, you wouldn’t. It’s a biz deal and she’s the one that should be spending the money up front, right? After all, she makes 2-3% on the transaction!

  8. Money Reasons

    I hate the battles around paying the bill. I put in my best effort to pay it, but I no longer get made if they other party insist on paying instead. It lessens the dining experience.

    Sexist or not, I always offer to pay the bill when I’m dining with women (even when they are wealthier and I am), it’s just my culture and honestly, expected most of the time.

  9. My wife is from the Philippines and her entire family is obsessed with paying the bill. They will do very strange things to pay including getting into a fight and grabbing match in public. It embarrasses me honestly, but I also don’t always want them to pay either.

    I admit I have snuck off to pay the waiter on more than one occasion because that’s the only way I can avoid a scene when I want to pay.

    What culture are you from Sam?

  10. Sunil from The Extra Money Blog

    i love it when women pay the bill – i am all for it. i just make sure i return the favor two folds in some form. that’s the man in me.

    but i don’t make much of this situation especially today when there is more equality than ever before. more importantly, women (at least here in the USA) are just as capable as men are to earn money, etc.

    as long as a relationship is mutually beneficial (you pick up some and i pick up some), i am good with it

  11. Let her pay sometimes. I am so fed up with this sexism of convenience, whereby it’s sexist to notice when a co-worker is wearing a nice new dress, say, but when you go for a restaurant or bar some women act like they’re monks who’ve sworn off money.

  12. New rule: If the other paying is charging the meal to their company or to the government, go ahead and let them pay.


    She could have billed it to her corporate account I think.


  13. Interesting how you describe how you grew up in an environment where there was competition to pay for the bill. I too grew up in a similar environment, where I saw my Dad yank the check out of people’s hands, make a deal with the waitress ahead of time, and just do whatever to make sure that he either A) paid the bill, or B) paid for at least our share. NO FREELOADING ALLOWED! It’s a matter of honor and self-respect.

    As for me, I’m just like that with the no freeloading part. I hate when people try to do it to me. My approach is that everyone should be responsible for their own share, but I’ll take the high road and offer anyway. I’m not as adamant about my Dad about paying the whole bill for everyone all the time, but I’m not far behind.

    I’ve experience people that have tried to weasel their way out of paying bills and EXPECT ME to do it, and I hate that. I just look at it as taking advantage of me on purpose. If I choose to pay the whole bill, that’s ok…but don’t expect me to or be shifty and steer things toward me paying.

    You can see that I have experience with these situations. My “Extractor” posts shares it in great detail.

    With the male paying for female bit, it really depends on the situation. In your situation, she should have seen that you were a potential client, and she should have either paid or made a strong effort to do so. Tells you something about her. Unless….she thought it was more of a friendly meeting, in which case I suppose you man up and pay…which you do anyway.

    Everyday Tips put it best though, it’s the person “wooing” who should pay. To me, this means early-to-mid stages of dating the guy pays all, and in business it’s the business that pays and the client/prospective client who doesn’t. That seems to make the most sense to me, anyway…though this is a topic that is apparently viewed all across the spectrum.

    Good topic…

    1. Yes, free loaders and those who weasel to get OUT of paying the bill are annoying. Like one of my friends who likes to go to the bathroom when the bill comes to NOT have to pay the bill! That’s weak, and so obvious.

      Perhaps I have a way for a woman to feel really comfortable when we go out, which may blur the professional line. I am VERY attentive when a woman is speaking. I make it a point to actively listen, maintain eye contact, smile and ask if she’s doing OK with food or drinks. Perhaps that’s what makes things blurry since perhaps some men are not like that?

      Nobody is wooing anybody. It’s just a friendly meeting over drinks to understand the real estate market. I guess friendships blur, so sometimes it’s hard to tell.

  14. I grew up in the culture where man always pays the bill. Now this being said… If you are her potential client (or so she thinks), she might want to pay the bill. And maybe you should let her. If it offends you or you feel guilty (sounds like your upbringing might have something to do with it), just pay for yourself. In the future, if we ever meet and go out to eat/drink (I love SF by the way), you will pay, and we both will be okay with it. :-)

    1. Sounds good. I’m happy to pay. I feel guilty if someone pays for me, but that guilt subsides if they are so determined and we plan to go again. Then, I will most certainly pay back the favor, no doubt about it!

  15. Steve Sildon@Credit Card Assist

    I’m old school like you …. pay the bill, regardless of who’s on the opposite side of the table. I absolutely abhor that feeling when the bill arrives. I was always taught to pay the bill NO MATTER WHAT. It has nothing to do with guy/girl, who called the meeting, who’s the prospect, none of that matters. You grab the bill and pay it. If the other party objects vehemently enough, for whatever reason, then I will relent. That never usually happens though.

  16. Investor Junkie

    ” In fact, even for new male acquaintances, I always pay the bill. ”

    So does that mean when we finally meet for Sushi, you’ll pay? :-)

  17. Ah, the infamous bathroom trick. My mother did that on a recent dinner with one of her friends and the rest of us family! Very sneaky.

    I can tell you that that is not one of the Asian customs I’m carrying on with, personally. It’s a silly charade. I do have one friend who is like that though – generous to a fault and always wanting to treat his friends.

    I was recently interviewing someone for a story over coffee, and assumed I’d pay for my own. However, when we got to the counter, he gestured and asked “What can I get you?” Which was a nice way of deflecting any potential conflict/confusion, I guess.

  18. haha that woman on Twitter could have a hard time in this day and age. Most people I know will pay for what they ordered, or divide a big bill evenly among the number of attendees for big gatherings. And if someone’s having a birthday then we divide up the bill so the birthday gal/guy doesn’t have to pay. Offering to pay for everyone’s drinks and meals is usually too big a bill to take on. However it’s much easier to treat if you’re only going out with one or two people, and that’s more common. I go for coffee with a colleague every now and then and we alternate paying for each other’s drinks which is nice and also saves time at the cashier. I think your generosity is awesome. I enjoy paying for friends and family. I always fight to pay the bill when I’m out with my mother. Even though she doesn’t have much money she always tries to pay because I’m visiting but I always grab the bill b/c I know she has a tight budget and she did so much for me over the years.

    1. That’s sweet of you to always pay for your mother. We kids should always fight to pay the bill for our parents. They’ve given us so much growing up…. like 22 years of their life and savings!

  19. The only person who owns your actions is you, if you let people on twitter determine how you should react in a public setting then your parents will have failed miserably.

    If you took the bill in my opinion it would have been proper for the other party to leave the tip. When I take out co-workers or my staff when I offer to pay for lunch or drinks I always let them know that I am picking up the tab but they are free to leave a tip. This helps them not feel awkward or like they need my charity to get through the day. On more than one occasion I have paid $60 for lunch and watched my co-workers leave another $50-$60 in combined tips. Since I live in a small community and work in a city of less than 250,000 this type of behavior is usually remembered the next time we visit that locale.

    Remember, it is always better to give than receive. You are living the golden rule, the only judgment you have to worry about is when you stand in front of St. Peter and are asked to pass judgment on yourself over the decision you made in this life.

    1. I don’t let anybody on Twitter determine how I react, although I do always enjoy the feedback and viewpoints of others. That’s some heavy judgement there! I don’t take it that far!

  20. If you paid because she has the opposite parts of you then it is sexist BUT SO WHAT. Why is it wrong? The society we choose to live in has certain customs and norms and you paying a couple bucks for drinks and dinner is just one of them.

    Does it make you evil that you are nice guy? Nope. Although you might be evil for using the spelling cheque rather than check. HAHAHAHHA

    1. Mate, “cheque” is the proper way to spell “cheque”! If you use “Check”, that just causes confusion!

      I would LOVE it if a woman insisted on paying everything for me. Alas, I’ve never met one out there yet.

  21. You’re OK.
    I also grew up and lived in cultures where paying for the meal is a form of hospitality. It’s an honor to have guests, whether in your home, or at a restaurant. Mere money should not be the issue. If you can’t afford the whole tab, you shouldn’t be dining out.

  22. If I am with a guy, I assume we will split it.

    If I am with a girl that is “just a friend” and I have no interest in, I usually plan to split it.

    If I am interested, or it is a date, I make a point to pay. If she protests, I am happy to split it. If it has been a longer term relationship, I don’t mind the woman paying some of the time.

  23. If she was providing information for you, you should pay. If she was marketing her services as a broker, she should pay. It did not sound like a social situation, unless you were hopeful!

  24. I guess I’m a little confused; were you a prospective client or was this a date? If you were a prospective client, I think she should have at least offered to pay the bill. However, if this was more along the lines of a date, I still think she should have offered, even if she knew you’d pay. I’ve been out of the dating loop for years, so maybe I’m just a bit rusty on this subject.

    However, when my husband and I go out with friends, we always offer to pay, split the bill, or my husband will “pretend” to use the restroom and pay the bill (he’s done this quite a few times.) We usually have to pull the “bathroom” trick when it comes to parents – they are so insistent on paying all the time that we have no other choice but to pull this little charade.

    1. Isn’t funny how just because se is a woman, people wonder whether this is a date? If it was a man, would feedback be different?

      This was simply a friendly mutual beneficial informational meeting.


  25. I don’t remember the last time I let the ladies pay the bill. I always say, let me pay this time and next time you can get it. That works pretty well for me. If a woman insist on paying the bill, that’s fine with me too. I never ran into that though, at the most they insist on splitting the bill. Usually it’s just me and the Mrs. and she does pay the bill sometime, I won’t argue.

    I also agree with Mike above. If I know I have more money, then I insist on paying. I do this when I go with my younger brothers for instance.

  26. I wonder who said on Twitter you are sexist for even thinking about paying? Obviously it must be a girl. And obviously that girl has some relationship issues or is lonely because I find it generous that you would like to always pay. Don’t let the negative folks out there tell you otherwise.

    And if it were me on the other side of the table, I would offer, and then I’d say drinks on me next time! So easy!

    1. On me next time really is the best way, even if there is no next time. I donno about the girl who said it. Makes me wonder, as if she’s offended by my questions, she must be easily offended by a lot of things. Gonna be a rough road for her imo.

  27. There really is no dilemma. Always be nice and offer to pay, whether you’re dining with a client or vendor, man or woman. (Client) relationship status and sex are irrelevant. Nice people offer to pay, unless it’s understood that they can’t afford it and it was clear from the beginning that the other party would be treating you. If you offer to pay but the other party insists on paying for whatever reason, don’t push your position, but you could suggest that they “get the next one.”

    And don’t expect someone else to pay just because of client relationship or sex.

    You just like to stir up controversy — but there really is no issue here if you just ask yourself, “What would a nice person do?”

    1. Ah, but you assume everybody is nice. Most are, but many aren’t and many have very strong viewpoints, which are sometimes foreign to me. Was she not a nice person for not offering to pay? I don’t think so.

  28. I don’t think it’s really sexist. You said you pay the bill. Period. Not that you always pay the bill for a woman. I grew up in the same type of environment – my dad is constantly sneaking off to pay the bill before his dinner companions even know what hit them. I always offer to pay when I’m out with someone.

    Now, I think it was really bad business for her to let you pay. Now, if she invites you out again to talk real estate, are you going to feel like you have to pay? You are the client. She will be making money if your business relationship progresses. Therefore, she is the one who should be spending money to get to that level. It’s also a tax deduction for her, but you’re just shelling out money. Bad form, in my opinion.

    1. Your dad rocks! From a business standpoint, maybe you are right that she lost some luster getting my business b/c I paid the $60 dollar bill. Yes, perhaps she should have offered to pay the bill or at least split it, but she did not.

      So I guess now, I have the “upper hand” where if I do business with her, she better hook me up with something good! But then again, I don’t think that way, and wasn’t thinking so that night. I was just happy to spend some time learning, and getting a ride home :)

  29. Sam.
    I don’t think that you’re sexist for wanting to pay the bill – it’s something that (like it or not) society has hammered into the heads of men (pay the bill, take care of women). I do understand the need for women to make it known that they can take care of themselves, but occasionally I feel like you pay a price for a kind gesture (like holding the door or offering to pay the bill).
    Because this was business, I thought that the person who called the meeting should pay (meaning her) because you’re her client (and it’s probably cheaper, because she can expense it to the company.

  30. One of the great double standards is that women would like they man to pay but may also subscribe to the notion that men and women are absolutely equal in every way.

    I prefer to think about it as not a man or woman thing but how forceful and stubborn the other person is. I usually end up paying for the other person, regardless of gender, if I feel that I have more money than them.

    That is probably the fairest rule (the most senior or richest person pays).

    So here’s to going out on a night on the town with Bill Gates.


    1. Mike, suppose the richest or most senior person weren’t you but the other person. Would you let that person consistently pay for your bill? (I wouldn’t.)

      RE double standard: in NW Europe you have pretty good equality between men and women, and splitting the bill is the common thing to do (or taking turns for the different rounds in a bar).

  31. If you are her prospective client, she should pay for you and write it off on her taxes. It’s the cost of doing business. Especially since you are truly looking to buy. She will make thousands of dollars off you after you buy a single property, so she “owes” you.

  32. Am I the only one who does not understand the dilemma? Am I missing something here? Are you asking who should pay a bill in a case where you two were out purely on business or were you two trying to get to “know each other?” If it was pure business, it should have been a definite split, male, female, or she-male :)

  33. It’s taken years to convince my wife, but she finally agrees that it’s not sexist for a man to open a door for a woman. It’s courteous. She even smiles when I make sure our 11 year old son holds the door for his mother and sisters.

    Paying? Meh. When I dated, I paid, but I haven’t been on a date since I was 19. When I’m out with friends, we pay out own way. There is a coworker I eat lunch with regularly. I pay her bill half of the time. The other half, she pays.

  34. Ha, ha, I’ve actually done the sneaking to the bathroom to reconnoiter with the server.
    If it were a date I’d offer to pay or split the bill, but I wouldn’t fight for it. I would also make certain to reciprocate in the future. If it was business or a new acquaintance I’d definitely cover my share and it the situation called for it, the full bill.
    I can’t imagine a considering a man sexist for offering to pay. No different than holding a door open. It’s not sexist, it’s considerate.

  35. I am more than happy to let a man pay the bill (although now it is generally just my husband, which means I am paying for it too…). I am also happy for a man to open the door for me.

    However, I always still offer to pay the bill, and the woman you were with last night definitely should have offered. With business, I think whoever is doing the ‘wooing’ (or initiated the meal) should be the one paying.

  36. Interesting post, as I rarely face this issue. Among my young professional friends, I always see us fighting over bills or at least assuming everyone will chip in. In more cases, if the bill is picked up by one person, it is the guy and it is probably more of “I was taught the guy should get the bill” type attitude.

    I do think if you have a job and want to go out, man or women you should always offer to pay your share and from there if the other person wants to pick up the tab, well its a win-win for both parties.

    I would like to throw another question out to the readers, around paying for Gas. If you are driving somewhere and offer another person a ride, show the passenger chip in for gas, even though you were going that way and had to get gas anyways.

  37. THinking back to my dating years, I can’t recall a girl ever even offering to pay the pill. Nowadays, as a banker, every time I go to lunch with a customer, its another dude (except for pretty rare occasions when the dude and his wife run the business together). I always make the first move for the bill since they are my customer, and I am almost always the one doing to the asking with regard to the lunch appointment. Most of the time I get push back, but I don’t give in, I just whip out a card, place it with the bill, and the conversation usually ends.

    I do think your situation last night was a bit different. Technically you were a prospect to her, so I would have expected her to at least make a move for the bill. This is a very interesting commentary. My understanding is that for business related meetings, the person who arranges the meeting, or requests the meeting should expect to pay.

  38. Money Beagle

    I’m a little confused because you said you met her at an open house, but then there was a bill involved. Your post didn’t really make clear that there was a follow-up meeting or something like that where a bill would have been involved.

    Anyways, assuming that there was some sort of follow-up meeting where you were gathering ideas and knowledge from her, then it stands to reason that you would pay, since she would be allowing for the courtesy of her time and sharing of information. That would hold true no matter the genders involved.

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