3 Lessons from Dating as a 40-Something

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Dating as a (young) middle-aged person can certainly be challenging and have its complications. I have been on the dating scene on and off for several years and I have tried all different platforms and ways of meeting people. For the most part, I would say it’s been a pretty pleasant experience and I’ve gained some pretty precious friendships in the process. But a few lessons have stood out in my mind and I can imagine many people who are 35+ and dating could relate. Here are three lessons I think have value to our core selves as we are looking for a serious life-long mate.

1. Find somebody who has the same ambition and zest for life as you do.

If I had to pick one main lesson that I learned, it would most likely be this one. For many people who are older, they found their groove and living their life as they want and now they’re just looking for someone to share that with. If that is you, then you were most likely looking for someone to walk beside you and enjoy the wonderful years that you have left. There are other people who are like me, who are just beginning a new type of journey. I am currently working on a new startup company with great ambition. I want to grow and learn about my passion. If you are like me, you need to find a mate who also has a similar level of zest and passion for life and wants to go on that journey with you.This other person does not have to be involved with every step of the way, but just someone who is on board to encourage and support you. And in the same way, if they are also working and striving for their own passion you can be there for them. This is what I want you to hear me say if you are a go-getter and have a zest for moving and making things happen…be sure you’re with somebody who will enjoy that ride! There are ways to know if it’s possible for them to do that. You need to ask this other person, what are their goals and passions in life? Where do they see themselves in one, three, and five years? If they can’t come up with any answers, or something meaningful for any of these questions, I highly recommend that you move on. No matter how much you love someone and enjoy their company, I would not make this person your serious mate. They definitely could be an awesome friend, but for a lifetime partner, you really need someone with a similar level of enthusiasm. Trust me on this one. In the long run, you will regret hooking up with a partner that lacks ambition and is not able to continually move forward and learn and grow with you. Many relationships end due to the fact one person likes to learn and grows on every level, and the other person is stagnated. Remember the saying that if you don’t stand for something you’ll fall for anything? The same for if you do not set goals and have a desire to continue to learn about a passion and to continue learning about yourself, you will then allow your environment and others to do it for you.

2. Never, never, never, never settle. Don’t ignore those red flags.

I’ve been on dates where I really liked the guy, and I chose to ignore all those little red flags. My go-to was to tell myself, that no one is perfect. And of course, that is very true. However, if something continues to nag you, in the beginning, this little deal only gets bigger and bigger as time goes on. You must know what you want and need in a relationship and you have to define the lines of many things and have a flexible line on others. If you do not, then stop now, and write down and make those lists. It’s very important if you’re going to seriously look for another partner to know what you want. Again, if you don’t know what you want, you are left wondering around the masses of others who don’t know what they want. If you’re simply looking for someone to date to enjoy company, that is a different situation than looking seriously for a mate. Looking for a serious partner, know exactly what resonates with you, and then you will recognize the good vibes in the other person. 


Trust your gut. Over and over I have proved to myself that those little flags or nagging in my chest do mean something. I finally got to the point where I no longer ignore those and that has led to much better dating experiences and saving my time. Also, saves on heartaches. If you think back to your last heartache/s you can probably pinpoint red flags that you left unaddressed. In order to have a fulfilling relationship, we must share and give of ourselves and in return be trusted with what the other person is sharing. It is a giving and refilling process. If you feel drained in a relationship, that is a red flag. Treat your time and energy as gold.

3. If it cost you more than you have, and you are not readily refreshed, stop now.

The truth is every single action we do, has a cause-and-effect, or a cost to pay. A lot of times this cost is simply our time, but time has value. We make choices depending on our environment, our situation, the people around us, how we’re feeling, etc. In exchange for one thing we either give time, energy, thought, resources, or money. Much time and effort are put into meeting people and then maintaining a relationship. Again, if you do not have your thoughts and wants and desires lined up, you can end up wasting many resources in your effort for a relationship. So, when you meet someone, and it simply doesn’t click, or you have a bad vibe, or timing is a factor, be brave enough and move on and forward. Not only does this cost you precious time, it’s also unfair to the other person. Wise dating means you calculate the cost of what you’re getting into. Not only could your time mean money, it can also cost your conscience, by staying in something you know won’t work, and it could cost you some reputation, by being that person who hangs around until something better comes along. Respect yourself and the other person to not behave that way.

Dating, and building any sort of relationship for that matter, it’s a learning process. Tomorrow is a new day for every person, and therefore we have no idea what it would bring, what new experience will feel like, and what we learn along the way. A big key factor is to know when you are seriously ready for a real exclusive long-term relationship. Each relationship that we have in our lives has taught us something about ourselves if we listened. At times it just takes patience and timing for us to get to the place where we know, love, and care about ourselves. When we can get to that place then we’re ready to walk with someone else to share each other’s experiences. And that is the ultimate goal; to love and be loved.

I wish you life true love and aloha.

Jessie xoxo

3 thoughts on “3 Lessons from Dating as a 40-Something

  1. Such a thoughtful and thorough blog post from the heart. There is gold here that resonates ones inner truth. Much to reflect on and appreciate. Thank you for this.

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