Love After 50: From First Date to Engagement

How do you become more emotionally available in dating? In this episode, we discuss some simple steps you can take today.
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Listen to the story of Kat and Shawn, a couple who met in their mid-50s. I worked with Kat before, during, and after she met Shawn, and they are a living example of how to find love after 50 and make the relationship work. They are engaged, living together, and navigating every up and down that comes with relationships later in life.
In this episode:
- What makes a relationship after 50 work well
- How to design healthy partnership
- Obstacles that come up in relationships and how to work through them
- How to know if they’re the right one for you
EP 697: Kat and Shawn – Falling in Love After 50, The Journey From First Date to Engagement
From Kat and Shawn
“We met online in our mid-50s, and the chemistry and compatibility were amazing from the start. We both value good communication and personal and relational growth. When we find ourselves at a crossroads, it’s extremely helpful to work with Sandy. She’s able to hear and understand BOTH our perspectives and helps us consider alternative ways of seeing our challenges. She gives us the tools to continue to build a healthier relationship.
We return to these new insights frequently and appreciate how much better our relationship is with the addition of an expert. She recently helped us overcome a big issue that was keeping us stuck. Later that day, on August 5th we got engaged! We’re grateful for a relationship that feels secure, loving, and supportive.”
Kat and Shawn
Highlights from the podcast
Tell us a little about your past relationships before you two met.
Kat: Divorced twice, running a business, raising two kids. Took a long time off of dating until kids were in college. Used to date guys who shared common interests. Hired me to be more intentional
Shawn: Divorced seven years, dated on and off. Stopped dating a bit before meeting Katherine. Didn’t have a high level of self-awareness or a partner with similar values before meeting Kat.
How did you meet?
Kat: I reached out to Shawn on Match and met for coffee. We were together for ten minutes, then met for a walk the next day. There was chemistry right away, and I had to intentionally slow things down.
Shawn: We had communicated for about a week before meeting, and there was instant chemistry when we met. I loved her humor. So I asked her out again for the next day.
How have you designed your partnership?
We have calendars and schedules. We are our favorite people to be with, but we also make sure to have time outside of the house on our own. We have a travel calendar for travel together and apart. We try to balance all of that. We talk about finances and long range goals.
What are some of the obstacles you’ve faced, and how have you overcome them?
Kat: Slowing down has helped us create a strong foundation to overcome obstacles.
The first disharmony was when I was in Africa for three weeks. It brought up insecure feelings in Shawn. Our insecurities are at the heart of every roadblock.
Shawn: Saying you have insecurity is much different from feeling it. We prioritize honesty above all things. And we agree that omissions are dishonesty. We own our insecurities. We first look at ourselves and ask if it’s something from our past or our triggers.
How has your relationship evolved over the past two years?
Kat: We repair quickly. We try to talk things out as soon as possible. We pray together daily. One of us is always showing up for the other. We have a white couch that we call our therapy couch where we talk everything out. We even created a breakup plan so we have guardrails on our relationship and will seek out three therapy sessions before making a decision to break up.
Blending our finances was challenging. I come from fear/scarcity and Shawn comes from an abundance mindset. I had to challenge childhood beliefs and communicate my fears to Shawn. We both have our teams for support which sometimes is more helpful than speaking to each other.
Shawn: I speak to other men who are committed to their partners, men who will call me out on my BS and be very honest with me.
What are your final words of advice for anyone who wants to go on their last first date?
Kat: What worked great for us was to take things really slow physically. I had a schedule about what was and wasn’t allowed, so the chemistry wouldn’t cloud my judgment.
Shawn: Early on, rigorous and deliberate honesty. Share things that you’re not proud of about yourself. Find a reason to be as honest as possible. It’s one of the most important things you can do. I learned so much about her when I was brave and shared with her.
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