Unexpected Break Ups with Jenn and Rebecca


I’ve spoken in the past about relationships and money, but it’s typically been around married couples and how to handle finances as a married couple. Today I’m talking about how someone you’re just dating can impact your finances and how you can prepare and protect yourself financially when you’re dating someone. Joining me to discuss this topic is Financial Gym trainer Jenn and her client and podcast listener Rebecca. They share their personal stories of love, loss, and recovery and how their finances were impacted because of it.

What Are We Drinking?

Jenn — Alka-Seltzer Severe Cold and Flu tablet with ice water

Rebecca — Moscow Mule

Shannon — Z Alexander Brown Uncaged Cabernet

Podcast Notes

  • Jenn is a trainer at the Financial Gym and Rebecca is one of her clients.
  • Jenn joined the team at the Gym in January 2018, as an apprentice behind the scenes. Her friend was a client of the Gym and knew Jenn had just left the hedge fund industry and was taking some financial exams to figure out the next step for her career. Jenn left her job without another job lined up, but she had an emergency fund ready to go with one year of expenses.
  • Jenn’s friend said she could see Jenn working at the Financial Gym. Jenn met Shannon and the team and fell in love with the concept of the Financial Gym.
  • Rebecca is in her late 30s and she lives in Jacksonville, Florida. She moved there from D.C. a few years ago to be closer to her family, and she is a long-time podcast listener.
  • Last year, Rebecca was on a journey to up-level her life and to get smarter and clearer about the things she wanted. She went through a bad breakup at the beginning of the year that really shaped her focus for the rest of the year.
  • She started focusing on what sort of partner she wanted and what sort of woman she wanted herself to be, and part of that was becoming smarter financially. She is great at making money and saving money, but she knew she could do more. 
  • She started working with the Financial Gym remotely. The Gym works with clients in 47 states and in D.C.
  • This past summer, Jenn and her long-time boyfriend broke up and Bridget and her boyfriend broke up.
  • How do you prepare for the challenges of a relationship when you are not married?
  • When you are coming out of a relationship, you are not thinking clearly. It is good to have someone who is objective, like a Financial Trainer.
  • Jenn was in a relationship for over four years and they lived together for a year. It was time to renew the lease and she found out that her boyfriend wasn’t ready for a commitment. They did not share their finances or have any joint accounts, but they split the bills down the middle. They did not have any formal agreement regarding financial decisions. Her boyfriend kept the apartment, since she couldn’t afford it by herself.
  • After the breakup, Jenn had the expense of finding another place and paying for a security deposit, and she wasn’t planning for it. She had just built her emergency fund back up when she realized she needed to move.
  • Many warm-up calls at the Gym are with women who are in bad relationships and need to get their finances in order so they can move out.
  • It is critical to have an emergency fund. There are no guarantees, even if you are in a great relationship. When stuff blows up suddenly, there are a lot of expenses.
  • Two weeks after the breakup, Jenn stayed at her friend’s place while her friend was on her honeymoon. Do you have family or friends you can stay with if a breakup happens?
  • Rebecca was with her boyfriend for three-and-a-half years and they were on the fast track to getting married. Two weeks before he was supposed to move in with her, Rebecca found out that he had been cheating on her for more than half of their relationship. She caught him through a series of texts, emails, and nude photos. She didn’t think he was capable of cheating.
  • Rebecca broke up with him in 2017, and she thought she was going to get engaged in 2018. Her boyfriend had asked her dad to marry her and was having a ring custom-made. 
  • Rebecca told the woman’s husband.
  • Moving on is a choice that we make. Once you choose to move forward and stop fixating on the awful things, you become much more productive. 
  • Rebecca first took an STD test and sent her ex-boyfriend a bill for it. Then she found someone to take her boyfriend’s place on the trip they were supposed to take together to England. 
  • Over the course of the next few months, Rebecca then started asking herself questions about what boundaries he crossed, where did she settle in that relationship, and what could she have done differently. She talked this through with herself and with a therapist. 
  • Rebecca used therapy and acupuncture to get through the break up, which was an unexpected cost. There were a number of other expenses that came up, because when she bought her house, she expected to have her boyfriend there to pay for half of the mortgage each month as well as some projects they talked about doing together.
  • A break up can happen to anybody at anytime. Stop and think about what would happen if your world was turned upside down by a relationship ending. What would you do and are you ready financially? Are you prepared?
  • “You’re never powerful in life until you’re powerful over your own money.” – Suze Orman
  • There is a grieving period you go through after a break up that costs money.
  • If you are in a dating relationship and you are thinking about moving in together, think about if you can afford the apartment on your own if the relationship ends and you can’t get out of the lease. Have that conversation internally before moving in. Make sure the other person has an emergency fund, in case they lose their job.
  • Don’t only think about what you can afford, but what could come up. Take a self-assessment of where would you be if things happened, and believe that anything is possible.
  • There is a light at the end of the tunnel. You are going to go through some really awful times and painful introspection. If you use those times as a learning experience, in a year, you are going to feel like a better version of yourself. You will realize that life can be bigger and bolder and better than you ever thought it could be. You can be in control of your finances.

Takeaway: My biggest takeaway is that relationships are unpredictable even under what seems to be the best of circumstances. It’s important for you to be financially prepared for any outcome, because the greatest relationship that you will have in life is the one you have with yourself. 

Random Three Questions

  1. Where is a place you would like to go, if money wasn’t an object?
  2. What is a show you like to binge watch?
  3. It is your last night on earth. What is the final meal you would eat?

If you’d like to talk to someone and have them help you prepare for anything financially, I hope you’ll reach out to us at the Financial Gym. My trainers have literally seen it all so nothing will surprise us. We don’t care how you got here, we just care about getting you where you want to go.

As many of you know, at the Financial Gym, we increased our rates in 2019 for new clients, but I have instituted a 15% discount for Martinis and Your Money listeners going forward so that the new rates will not impact you. So if you’re ready to manifest your dreams in 2019, which is our theme at the Gym, head over to or send friends to, financialgym.com to get signed up today.

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