Should You Ask Her on A Date? Do These 3 Things First

As any financially prudent person would do, at the beginning of each new year, I review where my discretionary income was being allocated.  I can understand trends and adjust to make better financial decisions the following year.  Understanding where your money goes will really tell a lot about yourself.

2016 was particularly active year for me dating wise since the divorce, but I ended the year single, and while the experiences I had were ones I’ll always remember, I would much rather have the money back in my wallet, if I’m being honest.

  1st Date 2nd Date 3rd Date 4th Date 5th Date
Girl A $41.64
Girl B $49.30
Girl C $80.00 $137.25 $99.82
Girl D $119.11
Girl E $11.90 $24.02 $10.59
Girl F $62.66 $83.22
Girl G $81.32
Girl H $61.94 $23.40
Girl I $21.00
Girl J $39.00 $33.92 $51.94 $26.97
Girl K $60.00 $38.41
Girl L $23.69 $108.55
Girl M $40.60 $33.00
Girl N $23.08
Girl O $100.00
Girl P $66.47
Girl Q $53.90 $30.33 $38.45 $50.00

Totals                 $935.61              $512.10            $200.80               $76.97

Gentlemen, if our math is correct, the final number should be $1,725.48, and if I’m being truthful, it’s probably more than that, if I broaden the scope to other women related things (clubs, strip clubs, etc.).

If I’m being candid, it was painful searching through my statements, knowing exactly what date I was on, with what person . . .. OH MAN, I REALLY SPENT over a GRAND, CHASING TAIL.

In all seriousness, those of you who know me, know that I’m the furthest thing from a player.  Intermediate game? Yes. I have some level of skill, but that’s not my purpose in life.  I was the kid that dreamed of being married at 12, the guy who at 26 wanted nothing more than to be married to the woman of my dreams and live happily ever after.

Anyway, enough about me, let us get into these numbers.  As you notice, the first date total is astonishing.  The average cost of the first date was $55.03, overall average cost per girl entertained was $101.49.  Just to give you gentlemen some perspective of what you are getting into.

I learned a lot in 2016, and I want to share just a couple important lessons with you, that are going to ensure to drive your costs down, entertaining women while you are working to become a high value man.

  1. Ensure the Person Fits the Mold


This is the most important rule and should be the most obvious; however, as men we are so attractive to the physical, we jump the gun only to find out later that this person isn’t what we are looking for.  I know a habit of mine, was in my introduction or initial conversations, I would bring up going out.  “. . . and I’d love to get up with you sometime soon” would be my ending lines.  Take it slow, have multiple conversations over the phone and get to know the woman.  No. I don’t mean “what’s your favorite color?” “What’s your favorite meal?”.  Ask her scenario based questions, questions encompassing the most important areas to you in a dating/relationship setting.

“If you have to choose between the greatest emotional connection with a man, or all the money in the U.S., which one would you pick?”

“What’s your relationship philosophy?”

“Are you an affectionate person or someone who likes companionship but wants her space?”

Weed people out ahead of time.  It’s much better to find out that a person isn’t for you over the phone or text, vs dates 1-3.  Open ended questions are great and brings depth to the both of you.  If you find out this dime isn’t an affectionate person, isn’t a conversationalist, or doesn’t seem all that engaged in general, move on to the next.

  1. Be Honest, About Your Situation


I am upfront about two things when I meet women: 1.) What I’m looking for 2.) My financial situation.  Reason being, I just want someone to know upfront what they feel like they can, and cannot deal with.  Let’s start with part one.  Having that conversation in the early stages (preferably before you take her out), will also save you a lot of time and money on both of your parts.  Why would you want to spend on a woman you want long-term, but she wants to play the field? or maybe you aren’t in a place to be in a relationship, and she wants you long-term.  Whatever the case may be, being upfront allows that person to make a choice.

Now part 2, you’d be amazed how fast a woman disappears on you if you mention the lack of funds, after you’ve already taken her out once or twice.  The funny thing about dating, is if you give your last for someone you like, they will be like, “well if you broke your mind shouldn’t be on dating”, however when you do have money, your efforts aren’t fully appreciated anyway.   They bring up wanting to be taken out, and still end up messing with the guy that only invites them over to chill anyway.

Just be honest.  If she likes you for who you are, she will stay.  If she is there for a meal ticket, or the only time the prospect of going out occurs is when you have the capital to do so, you’ll know quick to leave her alone, or she’ll leave on her own.

  1. High Value, Low Cost Dates


To piggyback off the financial aspect of dating, if you do find someone after talking to them for a while, that you feel fits the mold and are on the same page with, or if you absolutely can’t wait to take a person out.  Do something that will build the bonding experience at a low cost. Maybe you both like live music, walks in the park, coffee, ice cream, playing cards, cheap wine tours, etc.  Again, if she is into you, she’s going to want to do it.  Of course, you can jump the gun and invite her over, but that’s a high risk move that may not pan out in your favor.



In closing, if you notice, the underlying theme under those points is mutual interest.  The sooner you know your type, your interests, your mindset going in, and what you value in a relationship, the more efficient you will be in the dating process.  It may take longer to find who you are looking for, but it’s better to allocate resources to more important things, or the actual person meant to stay in your life long term, than to waste those efforts on the wrong person.  Now if you excuse me, I must see if I can write off the cost of these dates on my taxes.


Weather Your Storm, Maintain Inner Reign -E

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