Penny Smart Pound Foolish

by | May 14, 2018 | Dating Perspectives


I often find myself scrambling for ideas of where to take a girl out on a date, mostly since finances are tight and I don’t want a girl to feel any less special or appreciated.  My finances also impact my ability to travel for dating, to afford dating websites, and how I dress on a date. Perhaps most importantly, I’m often self-conscious about how I’m perceived by the girl I’m dating and my confidence in being able to provide for a wife and family someday. What can I do to maximize the success of my dating knowing that my finances are limited?


Finances are a sensitive topic for many people. Our Western culture influences us to wrap our self-worth in how much we make. The two most common questions we’ll be asked when we meet someone – “What is your name?” and “What do you do?”-  suggest worth based on career or earnings. This can leave us feeling down about how society or a date may perceive us.

It’s not just a dating skill, but a life skill, for us to continuously affirm to ourselves that an individual’s worth cannot be more divergent from the dollar amount on their paycheck.  Some people are extremely well compensated for minimal labor, don’t do much of lasting value, and don’t have much confidence in themselves or what they do. Others work day and night and struggle to make ends meet, yet make a difference every day, love what they do, and are happier people and family members for it.

In my coaching practice, I encourage people to look at the long-term sustainability of a relationship and making sure the focus is on whether relationship needs are being met.  When I hear a man or woman with an excessive focus on money too, I remind them how transient money can be. I encourage them to look for the character, connection, respect, and personality, that will be much longer lasting and more impactful on their wellbeing. It’s reasonable to have basic needs for financial stability. Marrying someone for money though can be a dangerous venture.

It’s also important to be aware that wherever you may fall on the financial spectrum, quality vs quantity will almost always prevail. What you may think you lack in finances, can be made up with many other strengths you possess.

Most quality women will be less likely to complain about the quality of a dating venue and more likely to complain that they didn’t feel their date was present, listening, or participatory in the conversation. Focus on creating a comfortable and enjoyable environment for your date even if the venue is simple. A woman is more likely to feel truly cared for when you invest yourself, not when you invest your money.

If you find yourself dating women that are particular about your after-tax earnings you may want to revisit whether you’re in sync on goals and values with your dating partners. Make sure that the material images of your future home and family are within the same ballpark. When financial expectations are disappointed, it can cause significant strife between couples and it’s almost always due to one or the other not fully disclosing and/or accepting materialistic expectations, needs, and abilities earlier in the relationship.

If you’re on a budget, pick dating options as your budget allows. You may find that singles events are the most cost-effective option. If you have had success on a dating website, stick with that to the negation of others. Trying every option at once is no more a guarantee of success than making careful and well-placed dating investments.

 It’s not just a dating skill, but a life skill, for us to continuously affirm to ourselves that an individual’s worth cannot be more divergent from the dollar amount on their paycheck.

There are also many low budget dating ideas. Here are just a few:

  1. Leisure walks on a boardwalk or downtown pedestrian mall
  2. A public garden or park
  3. Boutique coffee roasteries and shops
  4. Bookstores
  5. Museums
  6. Airports
  7. The zoo
  8. Bowling
  9. Miniature golf
  10. Scavenger hunts (for a bit later in your dating process)

To all the single Moms and Dads out there, this is certainly a challenge.  I empathize with the squeeze you experience being caught between parenting and trying to move on with your life. I and pray that it comes to an end for you very soon. It’s tough to support children, maintain a household, pay for dates and babysitting costs, remain active on websites and at events, attempt long-distance dating, get dressed up with your hair and nails done, only to come home disappointed and deflated.

I would recommend that you single parents team up with each other and try to take turns watching each other’s kids when the other is on a date.  You may also need to be a bit more discerning about who you date to make sure the time and expenses are justifiable as opposed to taking the approach of “Hey you never know…I’ll give it a shot”.

There are certainly options for lower cost clothing if you have a discerning eye for sales and style. You may have a friend who is blessed with good taste or a touch for online shopping and can guide you appropriately.  Invest in a few quality items which can be matched with each other and reused time and again. For long-distance dating, do some extra research and maybe try a Skype date first so as not waste time and money for a date that could have been avoided.

A Word of Caution: I would recommend that one consider postponing dating if they do not have a job or plan of how to support themselves and their family. Circumstances may be different if there is family support while someone is a student, learning in Yeshiva, temporarily between jobs, or is soon to graduate and begin work.  A man or woman without career initiative likely needs time to work things out and become comfortable assuming responsibility.  Someone experiencing long-term unemployment may well reconsider dating until he/she is in a more stable position.

As a final word, remember we are only looking for one…the right one!  The right one will deeply respect, value, and appreciate your unique and multi-faceted qualities, finances aside.  If they don’t, they are definitely not suitable for you. Boost your confidence through the consistent practice of presenting yourself on a date based on your internal and long-lasting traits as opposed to a dollar amount. May that true inner self attract the right partner and guide you the shortest route to your longest relationship!

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