Ask Single Dating Diva: Dating Broke Women

Not too long ago I wrote an Ask Single Dating Diva piece called “Dating Broke Men“. It generated much discussion on Twitter (inspiring some chats) and I received a number of emails and communications asking me about the other side of the coin … namely, Dating Broke Women. Traditionally, men should be the ones who pay for everything shouldn’t they? Perhaps. But, times have changed. Especially since a lot of women make good salaries, even higher salaries than men do. However, even if men step up and pay for things does that give the right to women to take advantage of their generosity? If a woman, broke or not, expects men to pay does that make them greedy? Let’s discuss …

dating broke womenDear Single Dating Diva,

I read your post about Dating Broke Men and it’s all well and good, but, what about broke women? I’ve dated some of those too! There are a lot of greedy women out there. They expect men to pay for everything all the time. All they seem to want are materialistic things – buy me this and buy me that. What happened to their OWN money?

These women won’t date someone unless they have money to wine and dine them and buy them whatever they want. Some women even just date in order to be taken to nice restaurants and events. I like to be a gentleman and don’t mind paying for things, but there has to be a balance. So what are your thoughts on that?


Not So Broke Man

Dear Not So Broke Man,

Thank you for your email and your question. I know that it might seem that “all women” are like that but that’s not true at all. Not all broke women are greedy and not all greedy women are broke. Most women just want a man who has his act together, a man who has a job, a roof over his head and willing to work together with his partner to make a good life for himself and his family.

Personally, after my divorce I was broke and struggling but I certainly didn’t expect or want any handouts. Now that I’m on my feet I would like someone who is, at the very least, at the same stage of life as me. I’m in my 30’s, so the expectation is that the man I’m with have his act together, just like I do. It makes sense to me. I don’t want a man who is just starting out or struggling financially. I want someone who can share the same lifestyle as me, who can afford to eat dinner out, travel and go to events. That doesn’t mean he has to pay for me but he has to be able to afford it. I had a different mentality in my 20’s, I was OK to build a future together with my partner. Now, I just want to enjoy life. Am I greedy? No, I don’t think so. I consider myself practical. Are there greedy women out there? Yes, of course there are. But, you can’t generalize.

Dating Broke Women

Ask-Single-Dating-DivaWomen also need to have more realistic expectations. We can’t all have wealthy partners who will take care of us. But, some women actually are broke. They have limited funds for whatever reason, perhaps they are single mothers, perhaps they are in school or maybe they just lost their job. Whatever the reason for it, they are just plain broke. Does that mean they can’t date? No it doesn’t but they also shouldn’t expect a man to pay their way. It’s not fair. Anytime a woman goes on a date she should always make sure to have enough money to cover her costs in the event that he doesn’t pay. If a broke woman really wanted that sort of “arrangement” then they need to find themselves a sugar daddy who is happy to pay their way willingly (for his own, ahem, fee). Otherwise, women should never expect anything from anyone. It’s just plain greedy! Like that woman who serial dates men that only take her to expensive restaurants she wants to try. Just because she’s attractive she feels that she’s entitled. That’s greedy and unfair and gives a bad name to other women!

It’s also up to men to spend responsibly. I realize that going on many dates can be very expensive. That’s why I always suggest a coffee or a drink be the maximum for a first date. Once you know you would like to continue with them, then, you can start spending a bit more money. Don’t let a woman take advantage of you. If you want to treat them to something nice then that’s your choice and you shouldn’t hold it against them. Some women would argue a man prefers a “needy woman” rather than a woman who has her shit together.

Traditionally, I would say that yes, men should pay for at least the first date, perhaps more, but women shouldn’t expect it and should always say thank you when men do pay because really they don’t have to. If a woman is demanding and asks for material things from you early on then that’s a red flag. A woman should be polite and gracious. If a woman “talks big spending” and she doesn’t have the funds to big spend herself, she might just be looking for a big spender. Beware the big spender!

Men, remember that not all women are greedy and out to get your money. Just like not all men are pigs who only want to get you in bed. Just date smart and choose wisely and that will increase the likelihood of you meeting someone who’s just plain normal and who’s on the same page as you. Imagine that!

In the mean time … enjoy one of my favorites ๐Ÿ˜‰

Your Sister in Dating Bliss,

Single Dating Diva

Copyright Single Dating Diva


  1. You know it’s interesting, as I’m one of those guys that feels it’s proper to pay for the first couple of dates. In my last relationship, I ended up paying for almost all of the dates. There was a few times where she said, “You know I could pay for some things… ” but it never seemed to come up during, you know, the time you’re supposed to pay for things.

    So for your readers, here’s what would’ve made me more comfortable to allow her to pay (written in the perspective of a fairly old-school guy in these matters… and again, this suggestion comes after several dates, I know I’m in for the first few/several): I would’ve preferred if she’d said UP FRONT before going out something like, “Hey you’ve gotten the last few dinners, when we go out to dinner tonight, I’d like to pick the tab.” This the is a good signal that she should control how much she’d like to spend on dinner.

    Anyway, food for thought.
    “Henry” (aka @DivorcedD20… but you know who the Real Me is ๐Ÿ˜‰


    • Thanks for the comment, personal experience and suggestions! Financial spending in a partnership should be balanced and it’s up to both partners to take responsibility. After a few dates I will make dinner at home for my guy and believe me that has more impact than going out, it’s good for guys to do the same. There are always solutions.


      • Oh, I’d have loved for her to make me dinner. She heated me up some frozen pasta a couple times… ๐Ÿ˜‰

        I’m actually quite the chef (well, BBQ’er anyway)


  2. interesting post , i personally believe that women can pay for dates. It really just has much to do with the ego probably, and what she’s thinking in her mind like: “oh no, if i pay for this will he not take any initiative from now on? or maybe he thinks this is ok, all the time?” i can imagine a woman thinking like that, but if the two of you have positive energy and are self actualized, and not holding on to old crap ./ emotions, then small things like this don’t matter much. just my 2 sense.


    • Thanks for your comment Khnum … people just do what comes naturally … share the costs of dates and/or be creative with your dates, some of the best dates I’ve been on have cost absolutely nothing!


  3. I do not know if its an appropriate place to respond to Not So Broke Man, but why the hell sir are you getting attracted to the type of girls who only treat you as an ATM? After all dating is first about romantic feelings, not only wining and dining and going to the most expensive clothing shops. If a woman is really interested in you, not in your banking account she would gladly spend time with you on a green lawn, having a pleasant conversation and nibbling on a chicken wing. If you don’t mind, take a tip: do not boast your money, tell your date about yourself and show interest in her preferences; instead of going to the 5 star restaurant, take her out to the picnic spot, do not try to sound clever, just be yourself and in no case bring a bunch of 200 red roses with you to your first outing together, rather a single, beautifully wrapped in a ribbon flower. From her further reaction you can judge, if she is genuine or fake diamond to incrust your family crown with. Well, i think i am going to far, when speaking of you family plans:) In this case just enjoy your time with the lady, who perfectly understands you and feels like your soul mate.


    • Thanks Diana. Often times when we’re trying to impress someone we make these big gestures, but in all seriousness it’s not necessary and will only give off the wrong impressions. There’s a lot to be said for being yourself.


  4. I’m not so concerned with ‘gold diggers’ or women who expect men to carry them. Maybe because of my age group or regional demographics. I find most women I date are willing to pay their half of the bill. Another reason I don’t worry is I don’t have the resources to carry someone, so it makes the point moot.

    I think we are in a period of change that is causing some frustration in the dating world. Women are demanding equality in the board room, as they should, but are also clinging to the anachronistic idea of chivalry. In short they want their cake and eat it too. That’s a rather glib idea and I think the truth is somewhere in the middle.

    I don’t feel an obligation in 2013 to pay a woman’s way. Some women I date make much more money than I do. Sometimes I do pay for a date,because if I am interested in a woman it’s just a nice generous thing to do. I want to demonstrate I am flexible and sincerely generous. And I think this point is an important one. Men sometimes pay not because they are generous. They pay for the wrong reason. That reason of setting up an imbalance. They have paid for diner, now there is an implication that the woman must reciprocate somehow. This is the wrong reason for a man to pay for a date. If they are paying for a date it has to be done with expectation of receiving nothing but a simple appreciative thank you.

    I recently when on a third date with a woman where things were going very well. This woman makes roughly twice the amount I do. The local symphony was giving a free start of season concert in a museum. It was a great event. I followed up with an invitation to go eat. She said yes, and we headed to a well known pub. I offered to pay. First of all I ask if it’s O.K. to pay. To me, just grabbing the bill without my date’s input is in bad taste. It’s making an assumption. I think it’s just rude. Some women simply want to pay their half. This avoids them feeling any obligation, as noted above. Secondly I pay attention to their response. If they act surprised that I even ask and were just expecting me to pay, I generally won’t date them again. Third, the best response I like is they offer to pay their half, but say it would be fine for me to grab the bill. And that’s what happened in this case.

    This response is generally my experience. She was sincerely appreciative. What surprised me was she responded I was one of the first men to offer to pay. Which struck me as odd. I guess where I am at, is the man should offer if they are sincere, but shouldn’t pay out of a sense of obligation.

    Conversely, I was on a date a couple of years ago. The date said she was going to the washroom. She actually went and paid for diner. Was I impressed. Not at all. I was sitting on the fence, and this just made things awkward. And I thought to myself this is how some women must feel when the man insists on paying.


  5. My thoughts on this are pretty straight forward. I pay this time, you pay next time. If things don’t fall into that kind of balance pretty quickly the relationship obviously isn’t for me.


  6. While I agree with a few things, in general, I disagree with this article and the stance you’ve taken, darling, but here’s why (and maybe I’m a unique butterfly or something):

    I am a single parent, and I don’t have ANY expendable cash. I wouldn’t be able to justify buying myself dinner in a restaurant, let alone pick up the tab for two people. So when someone takes me out on a date, the fact that that date is even HAPPENING is because the man is willing (and happy) to pay.

    I’m just as happy grabbing a slice of pizza or sharing a plate of nachos as I am in an expensive fine dining restaurant, though, and I always make sure he knows that. I’m no gold digger. And ALSO…

    I reciprocate, but in a different way. This weekend was date #4 with an amazing fella that I really like. We’ve gone out twice for dinner (on his dime, but not to expensive places, he’s a working class chap like I am) and once for a pint after an event (he bought one round, I bought the next).

    This weekend, we decided that since Christmas is coming, we should look for less expensive ways to have a fabulous time, so I brought a great big bag of groceries and a nice bottle of red wine to his place, and made him a homemade meal of boeuf bourguignon (Julia Child’s recipe, which isn’t a cheap thing to make), homemade bread and a lovely charcuterie plate.

    I spent the same amount on ingredients for that meal as he would have spent in a restaurant. It was fantastic because it allowed us to hang out in the kitchen together for hours doing something really fun, then we had a fabulous meal, AND we have a lot of leftovers for our lunch today! Plus, he said it had been a long time since anyone’s made him a home cooked meal.

    Next weekend, we’re going to a movie (he invited me) and we’re going ice skating (I invited him, and will bring along a thermos of boozy hot chocolate).

    So he pays for dates, and I contribute to all sorts of things in unconventional ways. Are we equal, dollar for dollar? Not by a LONG shot – he makes more than I do, and I have a kid at home. This seems fair to us – we’re both giving as good as we get, in ways that are comfortable and affordable for us.

    So to women who honestly don’t have two pennies to rub together – you don’t necessarily have to decline dates unless you have enough to cover your share, so long as you’re honest and transparent about it, and so long as you go out of your way to reciprocate. Parity isn’t always financial, and money doesn’t buy happiness.


    • Thank you for your comment Jennie and for sharing your own personal experience and solutions. You’re right, there are always ways around it if you’re open and honest about it and get creative.


  7. I guess I come from a very traditional background.

    My dad and brothers have always paid for their ladies, dates, girlfriends or wives on dates. Of course, they never put up with any gold diggers, not for a minute, who would demand expensive restaurants or gifts.

    I think a smart man can easily distinguish a nice lady from a gold digger.

    My two younger brothers (we’re a large family) are in their dating years and feel very uncomfortable when their date tries to pay some or all of the bill. It’s not machismo, they’re very sweet guys. That’s just how we were raised.

    My experience in the dating world has always been the guy paying for dates. I have always offered to pay, especially when it was a new guy, I don’t want someone who doesn’t know me to get a wrong idea about me. However, this guys felt it was their place to pay for the date. Since I feel uncomfortable if a new date spends too much on me, I make sure not to order something pricey from the menu. Actually, I just prefer going for a drink or coffee.

    Once I went on a date with a metrosexual guy and he started talking about the bill. It wasn’t high, it was a casual cafe. I more than willing paid my way. I’m always prepared. My family thought the guy was really cheap, and probably wouldn’t make a good partner. It also killed the mood totally. We went from sweetly flirting with eachother, to discussing my half of the bill. He called me the next day and I think he felt bad about making me pay for a sandwich on our date because he said he wanted to take me to eat to a nice restaurant. The holidays were approaching, and that weekend I went up north on vacation with my family. When I got back I just didn’t feel like we would be a great match, so I ended up going out with someone else.

    Sorry, long post! I twisted my ankle playing tennis and I’m keeping myself busy writing and reading here.

    Good luck you all!


    • I should mention that the guy I went out with was not poor or broke. He had a great job, fancy car and all.

      I did date a guy who was going to grad school and didn’t have money to eat out. He wasn’t the type of guy to let a woman pay for his dinner on a romantic date, and it would have been weird for me too, honestly. I love to cook, so we would cook together at his place, quite romantic. By cook together I mean he’d chop the carrots. Soon after, he got a job and we’d eat out once in a while to modest but pretty nice restaurants. His treat of course.


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