Published by admin on January 4, 2016

Why Broke Men Shouldn’t Date


This post is for the guys–the broke guys.

(You know who you are.)

I confess. 

I’ve been guilty, myself.

As a “creative” type who grew up believing that society should support ME to support IT, I was never very motivated by money. Give me time. Give me freedom.

Those were my mantras.

Well, that was cutesy when I was in my 20’s and 30’s, but as one of my close friends and mentors, Eric Saperston, once told me, “Once you hit 40, you can’t rely on being cute anymore. You have to actually do something.”

Crap. That was a problem.

Me. Over 40. Lots of time. Not a lot of money. And therein lies the cruel twist: are you really free if you don’t have the money to enjoy your time?

The answer was yes for my 20’s and 30’s, but decidedly NO in my 40’s.

Now, let’s add dating and relationships to the mix. My experience has been downright embarrassing.

For a while, I tried to hide the fact that I was broke. It was always a coffee date. And you can guess my biggest fear as we walked up to the counter: that she would order something with the words latte or mocha in it.

I developed a strategy to overcome this potential money-trap. By a stroke of luck, I have a coffee shop in my backyard that serves french press coffee–for two.

Can you say, $4 date?!

I should have just named this post, “Coffee: the Poor Man’s Date.”

Anyway, here’s the real issue:


Guys. Yes–you can fake it for a date. Even people of means sometimes go on coffee dates. The real problem is what you do after the first date. Are you going to do coffee for date #2? and #3? At some point, you have to transcend coffee.

I’ve tried everything.

“Let me cook you dinner. I’ll bring all the ingredients.”

Now, this is a two-pronged strategy:

1) Save money by not going out (you can do a pretty nice, home-cooked dinner for only $10).

2) You’re already in her pad at the end of the night.

And, really…

3) If you’ve done things right, you’ve dropped by your local Trader Joe’s to get a bottle of 2 buck chuck in advance.


Game. Set. Match.

Ok, so I’m being playful here. I’ve done all of this. But in all seriousness, being broke definitely caused major difficulties in my last relationship.


Honey, can you look on Groupon to see what deals are going on tonight?

If we really liked a place, we’d use my iphone, skip a month, dye our hair, and then go back and use her iphone the next time around.

You getting the picture?


This went on for TWO YEARS!

She was frustrated, and I felt like shit. I would try to rationalize:

Babe, being an entrepreneur means making sacrifices.

Just you wait–we are going to be ballin’ in six months.

Yeah, right. Money was always a problem. Stress. Fights. Disappointment. Soon, borrowing money from your girlfriend: a recipe for disaster.

To the Men: I know what you’re thinking. You are not defined by the size of your wallet or bank account; you are special (like a snowflake). Yes! You are special! No! You’re not defined by the size of your wad (or wand). But if you try to date them… judge you, they will!

Let me remind you of something. You’re dating a WOMAN!

Someone who adds bountiful love and amazeballs to your life. She deserves to feel like a woman and not always have the pressure that comes with your broke ass always being broke!

Now, let’s be clear. This doesn’t mean you can’t get laid. You don’t need money to get laid. You also don’t need to fake interest in a relationship to get laid. All you gotta do to get laid is…


Novel concept. (**women nodding heads in agreement**) This doesn’t seem right, Alex! But trust me, young padawans, it’s true. There are many, many women out there who are, for a variety of reasons, not interested in a committed relationship. They are open to something physical; something playful.

If you bring bullshit tactics, however, your likelihood of getting laid will diminish quickly. It’s like trying to use a Jedi mind-trick… on a JEDI!

It doesn’t work.

Not only that, but you’ll never feel fully confident when you’re broke and dating; you won’t ever truly feel like yourself.

Now, if you want more than just a hook up, leave and get your shit together. Then, come back–but strong.

It’s like in The Matrix:

Neo (to Morpheus): What are you trying to tell me? That I can dodge bullets?

Morpheus: No, Neo. I’m trying to tell you that when you’re ready, you won’t have to.”

In other words, when you come back strong and self-sufficient, you won’t have to find a woman; she’ll find you.

To the WomenWhy?  Why do you allow this? You know in your gut of guts that this isn’t the way it’s supposed to be. Don’t you realize that you’re just enabling boy-men to remain boy-men? They will never change with you enabling them!

Yes, Women. I know we can be attractive to you.


Aka: Peter-Pan Syndrome.

So, here’s my suggestion:

Fuck us, but don’t date us.

You’ll be much happier.

And maybe by leaving us (for those of you who are currently dating a boy-man), you will actually help some of us to grow up and become the Men we really are capable of becoming.





































  1. Renee
    January 4, 2016 - 9:47 am

    ” Fuck us .. But don’t date us.” I’ll definitely remember that.

    • skyxander
      January 4, 2016 - 9:56 am


      • Renee
        January 4, 2016 - 11:28 am


  2. Geetha B
    January 4, 2016 - 11:13 am

    Lol, your post is very funny and a lot of it may be true but I think you are leaving out a great many fundamentals of which I will touch upon a few:
    1) Society has evolved and you guys need to face it. Women are CEOs or other big earners sometimes and they don’t mind having a guy who is broke or very close to that provided he is willing to take on the role that was traditionally that of the woman, in brief the cooking the cleaning etc etc. The problem is that most guys are not willing to take on that role or if they do, social pressure then gets the better of their nerves
    2) There are many men who are broke not because of Peter Pan syndrome but simply because they have faced difficult circumstances. Women are patient with difficult circumstances as long as it is not paired with a bad attitude
    3) Many women are willing to share the tab or even go out sparingly or use the great discounted deals. Usually, you would find that any fights or problems in relation to this are actually associated with the man feeling bad about the situation and reacting agressively or in a passive agressive mode without even realising it.
    4) Women will usually (unless they are only interested in the money either because they are gold-diggers or incapable of making it themselves) prefer a nice, honest and fun man to be with over a man who has a lot of money. The catch is how to make this transpire in the first dates without looking too weird and putting her off. I’d say honesty is the key yes but also a lot of humour. The only problem being that if you’re broke and feel bad about it, you’re going to have a tough time finding something humourous to talk about.
    5) Women might want to have fun at the beginning but at some point they usually do get attached which brings you back to square 1 in terms of the considerations of how to go about being broke so your solution for being broke should not be to just keep on f… ing around with women who are set on absence of commitment. Besides, as you grow older, your life becomes quite sad if you don’t build any lasting relationship around you. It’s quite awful to not have anyone at all to relate to. We are by nature and by social pressure conditioned to be in a relationship whether with the same gender or with the opposite. Some people replace that with a pet but a pet does not sustain conversation with you so it is a lop-sided relationship.

    In any case I enjoyed your write. It is quite funny and I had also enjoyed your previous write. I hope you’re not so broke for too long. Good luck with whatever business you’re grappling with and much fun for the upcoming year.

  3. survivednarc
    January 4, 2016 - 11:49 am

    Haha this was funny! This is why I follow your blog 😊 cause it provides a small escape from my miserable blog/life. Lol. Well not only that ofc, you had some other great posts (that were not on the funny side). Have a nice day.👍

  4. nazamwasi
    January 4, 2016 - 1:14 pm

    Oh my God! Finally someone says it! This is so true.. every last word!!

    • skyxander
      January 4, 2016 - 1:22 pm

      Wow! Thank you so much!!!

  5. Ask Cara
    January 4, 2016 - 3:08 pm

    Me and my best friend were just talking about this Saturday. A man needs to be stable if he plans on seriously dating someone, especially if the woman he is pursuing is stable. That’s a deal breaker.

    • skyxander
      January 4, 2016 - 6:32 pm

      Yes, 100%. That’s a really good point. Like what-are-you-bringing-to-the-table? haha

  6. Rabbittruns
    January 4, 2016 - 3:13 pm

    Very enjoyable read. A lot of honesty there i like it.

    • skyxander
      January 4, 2016 - 6:32 pm

      Thank you! 🙂

  7. Kristin Joy Currier Ludlow
    January 4, 2016 - 3:37 pm

    I love this. One thing I’d caution men against is to think this is *all about money*. It’s not. You don’t have to the BMW, sweet pad, power job, etc. Unless that’s the type of chick you want. But a quality woman wants a driven man up to big shit in his life. If he’s committed to that, “abundance” will come in every form, and your woman will trust you and want to be with you. And although I understand what is meant by boy-men here, I’ll be the first to admit there is nothing sexier than a man in touch with his boyish side – but who is also driven to be the best man he can be.

    • skyxander
      January 4, 2016 - 6:36 pm

      Very cool comment, Kristin! I love what you say about a “quality woman wants a driven man up to big shit.” That’s so great! I’d love to expand on that theme sometime. I think THAT really is the key: Women OWNING that they can create the standard(s) to which Men will want to rise to. I really believe that. That whole padawan-to-Jedi thing is like women seeing the “good” in men, and helping us to get there (even if sometimes in painful ways by rejecting us because you want us to reach our potential). Why? Because we’re all partners on this adventure towards something higher–our truest, most bad-ass selves! Wow! You really inspired me with this comment. Thanks again, and please keep writing! ~Alex

  8. skinnyandsingle
    January 4, 2016 - 7:18 pm

    You think I’m willing to miss out on a quality guy because he currently can’t afford to buy me a coffee? I’ll buy my coffee, and maybe I’ll buy his coffee.

    I’ll pitch in on ALL of our dates.
    I will make sure not to tax someone’s wallet just because I like them.
    I work too, I’m broke too.

    I will help.

    • Proudscousemama
      January 5, 2016 - 3:37 pm

      When I moved in with my now husband we went from having lots to being totally on our asses broke. That would be a deal breaker as well as a lot of stuff we have experienced together. But looking back and seeing two happy healthy kids and that we are still happily married it really does not matter. Money cannot buy love. You learn to love not earn it

  9. TWJ
    January 4, 2016 - 7:59 pm

    I think Kristen is on to something with “quality woman wants a driven man up to big shit in his life”. Additionally, her next comment speaks to a man being “settled”. Being “settled” provides clarity and I suspect provides most women a sense of security and confidence. Our world puts an inordinate amount of pressure on men “to step up and get your shit together” and that’s mostly represented financially (though being grounded in who you are and in your relationships I think is more important and has a more material impact on the quality of romantic relationship).

    In your past relationship, I suspect you weren’t “settled”. Being “settled” is another way of staying confident. If you lack confidence and she doesn’t see actions toward the fulfillment of what you say you up and committed to in life, you can forget about it. That’s not to say there aren’t peaks and valley’s however that women will stand by you through it all if you willing to do what it takes and be confident often with no guarantee of success.

    Confidence or being “settled” is directly correlated to the quality of your relationship. A man up to something huge, doing what it takes to make it happen, is in full communication, and has demonstrated great relationships with his friends and family will have a quality women before that man who has the wherewithal to whisk a women away on a weekend trip to some exotic location.

    In your last relationship, I suspect the context of your “Groupon dates” was survival not building something. You lacked confidence in the prospect of your success or ability to produce results. No difference for polyamorous relationships. It requires an incredible amount of confidence, and often the ability to create the same for others. Most people aren’t willing to confront their “shit” in order to have this type of relationship. They would rather blame the circumstances.

    I think this article more than any others only shares a very narrow view, and it any points to the underlying insecurity most men and women share. If you find a women committed to something bigger than herself (or her family, job, health), doing the work of personal development, and is in love with herself, I promise you stuff like “money for dates” will fall far from the top of any potential concerns.

    I request you write a follow up that goes deeper and speaks more to those conversations which make us all uncomfortable. Accept?

  10. Miranda
    January 5, 2016 - 2:45 am

    There are differences between being broke, being budgeted, and being a cheapskate. The first two can be worked with; the last one not so much. The “budgeted” man may not have a lot of extra cash, but he sets some aside to make a special occasion. The “broke” man has to be creative. Bike rides, hikes, picnics, etc. – all good. The “cheapskate” just makes things awkward and uncomfortable for a woman, because he TALKS about being broke ALL THE TIME. Stop that shit! It’s only an issue if the guy makes it one.

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