Love and Money: A Man's Guide to Not Going Broke While Dating

Scroll back the clock to 2017. I arrived at a museum in DC to catch a lecture from a renowned photographer. I stumbled into a friend. A short conversation ensues and she goes on to “fem”xplain to me that, “if Guys really wanted to date her and her friends, it would be just as simple as bringing them to events like these.”

There are many money-hungry women nowadays. Digging through the weeds will land you the right one but you are bound to catch some splinters. Dating sucks.

Fellas, those are unconscionable lies! And for your own sake, don’t tell her that, just nod and shake your head. A lot of women believe that we are battling legions of zombie women “the bachelor” style. That’s also a lie.

Having been on the dating scene during the transition from normal cold call conversations to swiping on Tinder; I can declare that dating is hard AF.

There are many money-hungry women nowadays (with all due respect). Digging through the weeds will land you the right one but you are bound to catch some splinters. I would also like to add that the majority of the stories that I will share, happened to a lot of people around me so take copious notes (note to self lookup copious later).

Bonus tip, man to man. You are 23+. Get a bible, a dictionary, and a thesaurus. And get the Fit Men cookbook. You have to know stuff. And for Christ sake, start investing for that sweet cash.

Table of Contents

The Failed FREE Date

We know all too well that a FREE DATE sounds amazing in theory, but in practice, it is entirely another thing. This isn’t the 1910s. You aren’t going to roll up on her with a walk in the park, a romantic montage while reading sonnets from Shakespeare, and expecting second base. If your beard game doesn’t connect, you have to work on things. And if you don’t have abs, you might want to be a sharp dresser with the comedic timing of Kevin Hart and Dave Chapelle (combined).

You have to literally entertain her like a clown.

The friend, fictitiously named Liz attempted to argue that men have it easy. Trust your instincts, that too is a fabricated myth and fabled legend told in women’s circles over two bottles of Trader Joe’s wine. Mad ramblings of wine drunks should be stricken from the records.

Just for kicks, let’s play along with the scenario.

You run into Liz.

She looks amazingly average but you give her the benefit of the doubt. It is Tuesday! You talk. Through blind luck, and maybe an assist from the Man upstairs, you get the number. Lifted by the whims of four saints, karma, and the universe, you were able to rally through an interview-style phone call for a date.

She shows up looking amazing (not a bad roll of the dice); you walk to the museum together for this FREE event.

The night is still young, and you are “seemingly” having a great time. You walk her to her car. You shoot your desperate shot for date #2. A week later, Liz is too busy.

A week after that, she ghosted you. A month later, you run into Liz. You talk for a few (minutes) and she states that “it’s hard to meet any good guys in the city”. Liz acts like it wasn’t a date at all. The curve is real.

While entertaining her two other prospects; here you are, Mister FREE event. Liz has been wined and dined by the best of them. The first was a known womanizer who flew her to Cancun to slide into Homebase until further notice. She was way too busy for you but wide open for him (wide). The Second guy, is a longtime friend from college whose shadow looms over the “Friendzone” forever. That guy drops at least $100-$200 hanging out with her all weekend, from brunch to day-party to the club. He acts cool but the dude is thirsty AF.

Your post-date breakdown with her friends started like this:

Friend A (aka Friend Prime): How was the date?

Response: We went to the Museum for this Free event.

Friend A (immediately 4-way calls Friends B and C). They proceeded to discuss your cheap a$$ ad nauseam. One, whom you never met berated your entire life. The other, who is in a long-term “Situationship,” chimes in that “you ain’t Insert Explicit Terms”.

Friend D, who appeared from her lair of bitterness via iPhone messaging, provided you with the moniker of a nice guy. She will never date you. To that I say, her loss. She was trash from the begin with. She did you a favor. I’m going to give you pro-level dating tips that were applicable as of 2017 (since I’m off the market). (see below)

1. The Rule Book Has Changed

There are many money-hungry women nowadays. Digging through the weeds will land you the right one but you are bound to catch some splinters.

Women make money so don’t let her con you for a free meal or her weekend entertainment. Value yourself. Choose a woman based on her values over her looks. Nine out of ten times, her hair isn’t real and her makeup is caked on. Guard your virtues. You don’t have to pay for everything anymore, but if you invite her, you probably should. It makes no sense to expect her to cover your invitation. According to USAToday (and some rich guys), the average cost of dating in New York is $297.27, LA is $226.35, Atlanta is $121.12, and Florida clocks in at $128.82.

“According to an analysis of 2,000 communities by a market research company, in 147 out of 150 of the biggest cities in the U.S., the median full-time salaries of young women are 8% higher than those of the guys in their peer group. In two cities, Atlanta and Memphis, those women are making about 20% more. …The new study suggests that the gap is bigger than previously thought, with young women in New York City, Los Angeles, and San Diego making 17%, 12%, and 15% more than their male peers, respectively. And it also holds true even in reasonably small areas like the Raleigh-Durham region and Charlotte in North Carolina (both 14% more), and Jacksonville, Fla. (6%).” Workplace Salaries: At Last, Women on Top, Belinda Luscombe, September 2010

Translation, she is likely making more money than you, so don’t do her any favors. Respect yourself.

2. Pick Out Your Battle Arena

Don’t let her choose. She will always go expensive. She says she doesn’t know where she wants to eat; odds are she is right but she keeps a shortlist of expensive restaurants that her friends told her about from other expensive dates. Go to your favorite eatery. If the date fails, you ended up donating to your favorite location. The bartender will notice a pattern and start to play as your wingman for the next 5 dates. It’s a win-win.

3. Develop Your Own Personality and Skill Set and You Shall Run into Her

There are great women out there. You won’t find them at home while you are watching Netflix. You can find them running. So join a run group.

They are likely writing the next self-help book at Starbucks or whatever new hipster coffee joint opening up soon. There are tons are women in a salsa class. Get to a salsa class ASAP. You will have fun even if you don’t know what to do. Give yourself a chance to learn and smile more.

It’s easier to run into her doing something you want to do versus taking her there for your intro date here. It’s the ultimate icebreaker. You can even go to a Toastmaster’s meet-up group. Many hotties end up there. Nerds are sexy.

So get over your public speaking fear. And, share this traumatic experience with someone that is going through the same thing.

Hi, insert name, I’m new here. How about yourself?

Women are looking for chemistry, assertiveness, and curiosity. They are looking for someone to take on life with. Here is the list of the things that really matter that you should improve to become an overall better person.

4. Don’t Cheapen the First Impression

I agree with the women in the example above a FREE first date was a cheap move. Never go free from Jump. That’s just bad form. Set a budget, even if it is just $20. You can turn a simple meet-up into a memorable occasion. I once took a date to a golf course at sunset with a bottle of wine and a movie on an IPad. Bring a light blanket and voila. You might want to take notes.

Don’t ruin your first impression. It’s not just a dating tip. This is a lifetime of value in one statement.

5. Group Dating Can Get Loud and Expensive

Avoid going out with her and her friends, it is a recipe for spending out of your wallet for double the drinks (minimum), two entrees, an appetizer, and dessert. All that and you can end up paying for the friend that always comes short. The place is loud. You will be competing for air time, looking like the Democratic Debates in 2019. The stage is too crowded.

Nine out of ten times, remember she might be doing this since there is safety in numbers. So keep it light, daytime light. Invite her to the matinee. Though movie dates can be risky; always spring for comedy or anything with the Rock. It might be ridiculous but at least it doesn’t ruffle feathers.

6. If She Turns Away When the Bill Comes Due and Says Nothing, Beware!

Not all women are saints. She is likely here for the free ride (I heard many stories). No date should really ever exceed $20, maybe $30 if you are feeling generous.

Set a budget for yourself. Do what you need to do to get out of debt and strategize yourself for a better future. The goal here is to recognize that this is just a date. It’s an intro.

Closing Remarks

“It’s not the one you spend Saturday night with; it’s the one you can spend your boring Sunday morning with, that matters.”

Dating is rough on both parties. Women spend a great deal of money to look the part. And you will spend some money to court them. In the end, if you can’t connect beyond the money spent, it’s not a real connection. Some of the best couples that I know, go running together. They go hiking together. They work at a pet shelter together. Be the best man, you can be. Show her that you are worth way more than just money. If you ever feel like you have to buy her love then you are going about this the wrong way.

For happiness and for health, cheers to finding the one.