Five Things To Do When Dating After Forty

Sometimes life throws us a few curve balls and we find ourselves in a place we never thought we would be. Maybe it is a divorce that has us reeling, or sadly, the death of a spouse. It’s possible that it just may have been the end of a long relationship, without the bonds of matrimony. However, whatever the reason that we find ourselves single, some of us decide that we are willing to throw ourselves back out into the middle-aged dating ring. Dating after forty is an overwhelming thought. We thought those days were over and we shake our head wondering how we are ever going to do this again.

Let’s face it, there could be several reasons we are putting ourselves back into the dating market. A market that we had long thought had closed, shuttered, and had gone out of business. Maybe we want a true relationship, marriage, or just a little nooky to keep us warm in winter. Whatever the reason, dating in our middle years brings about new challenges. I like to think that we have matured enough at this stage and are confident in who we are and able to handle the ups and downs of dating again.

However you begin the process of dating at a later age, online, through friends, or at happy hour on Friday night. If you are fortunate enough to get through the not-so-worthy and find someone you have a real connection. There are some things you should keep in mind.

My own experience with finding love after forty brought me to really understanding what real love is as well as how different love is  when you are no longer in your twenties.

Read more about that here: My own journey to finding love after forty.

1. Forgive the past.

You both have one.  Both of you have had years to have dated other people, been married, made mistakes. You may even have suffered loss. Regardless of how you arrived at the present, you have a past. Trust me, I know how awkward and irritating this can be at times.

It is possible to love more than once in your life, so accepting your partner’s previous loves as part of who makes them who they are now is important.  Let’s not forget, you have a past as well.

Your partner having loved others has taught  them how to love and how to be discerning in choosing a new partner in their life.  Likewise, it has taught you as well. You both know what you want and don’t want in a partner. It makes for less game playing which is a welcome relief for most of us.

That means you are now fortunate as you get to see the present as time where love is full and complete. You also get to share what you have learned from the past and be more open and honest. Hopefully your past has taught you both that honesty is real key to a successful relationship.

2. Be honest about your intentions.

I don’t mean tell him or her on a first date that you are looking to get married. Blurting out that line could have the other person run  just as fast as if they were back in college. All you may get from this is a trail of smoke leading away from you. However, realizing that now that you are older, changing someone is not possible. You cannot make someone want the same things as you. Been there, done that. Finding someone with shared goals for the future is important and being older we can do this with a more direct approach.

In our younger years we thought we could mold someone into our perfect mate. That was my big mistake. The mistakes of our youth do not have to follow us into the present. Be honest about what you want out of a relationship. Talking openly about what is important like honesty, friendship, and intimacy early on can help you find the path that will be right for the two of you.

No one wants to waste time with someone who’s goals in a relationship don’t line up with our own. 

 3. Don’t assume devoted time.

Kids, aging parents, busy work schedules mean a life with a lot to do.  Twenties and no kids was a time when you could be devoted to one another every minute of everyday. You had nothing but time to spend with each other. Those days are gone and you have to accept that in each other. Romantic dinner dates may be thwarted by having to go see your sixteen year old in her school musical. A weekend getaway is interrupted by his mother being hospitalized.

Sharing real life can make or break your relationship and can also be the stuff red flags are made of. You can see how the other reacts to life in very real time. Make sure you pay attention.

Someone who is miffed and irritated with life’s demands is definitely not someone you may want to continue to see. Being older can give us a very real window of what life would be with someone that we couldn’t see with those we chose when we were younger.

Sharing the sunset in our sunset yearscan be wonderful if you are prepared.4. Remember it’s never to late to love.

Never forget it is never too late to love. Don’t ever think you are too old to find love again. Always be open to the possibility of loving new people in your life. My Grandfather found love again and married at the age of ninety. He had four wonderful years of love and companionship in his last years. How marvelous is that? Just be open to the possibility and when you are ready, it will present itself.

5. Enjoy the present.

It is very easy when finding a new love to wish things had been different, especially if your previous relationships ended in disaster. Wishing our past had been different is just simply wasting energy and taking time away from the beauty today holds.

We can’t change the past. So now more than ever, you must live in the present. It is likely there are fewer days ahead of you then are behind you, I know, sobering thought. So make every day count. Enjoy the time that you do have knowing you are fulfilled and happy, not living with regret.

How are you joining the dating world? What is your strategy, successes, failures, insights? I want to know.

Reinventing Julie - a blog for the middle age empty nesters


About Julie Mason

Julie is a nearly fifty year old almost empty nester. Life is interesting, ever changing, fun, infuriating, and Julie wishes to share it with you all. She hopes to learn along the way as well and write about anything and everything that strikes her fancy.

41 thoughts on “Five Things To Do When Dating After Forty

  1. These Tips are great for anyone whatever the age, if dating and even married people Julie.

    People think that once you are married you stop dating. NO< You are now DATING ONE MAN/WOMAN thats it and you must date them, i.e. make em feel extra especial a lot of the time 🙂

  2. Love after 40 , well it sounds ok but for me it is too scary and uncertain to jump out there and I am way past 40. I am set in my ways and I like being by myself. As soon as my son goes off to college in a few years I plan to get a dog and relax finally. If love finds me ok, but It is definitely not a priority.

    1. Knowing yourself and being able to be firm in that in your choice of a new partner or not is really the whole point. I had no desire after a divorce, and accidentally found the greatest love of my life. Ya never know.

  3. I met a man two years ago when I was 70 and he was on holiday. He had lost a partner of 38 years and I had been divorced and had lived in Spain for 10 years. We are now living together ( for 19 months ) and are planning to get married after he proposed in May this year. We have been on wonderful holidays, to Cuba, America and the romantic sights in Rome to name but a few. We are off on a cruise to the Caribbean shortly, making the most of what time we have left and every day we love each other more. Never give up on Love, no matter what exoerience you may have had in the past.

  4. Wow Julie this post hit home with me. Although I am not divorced, and have been with my husband for 23 years, it has not been without it’s share of ups and downs- including that fact that he is bipolar and not in treatment. Now that we’re quasi-empty nesters, we are slowly rekindling out marriage. It takes a lot of work. It’s not pretty and it is lonely at times. But this is my life and I am accepting it. The tips you mention can also be applied to the middle years of marriage, because they certainly will help with mine.

    1. I’m so happy you have benefitted from reading this. I makes me happy when anyone, even an audience that was it was not directly directed to, get something from something I right. Keep wprking at it.

  5. These are great dating tips. I ended my engagement in my late 20’s and started looking for a serious relationship in my early 30’s. It was definitely different than dating in my early 20’s, as I knew what I wanted and was more set in my ways. Luckily, I did have luck and found my husband, but we did both have to get by our pasts, as well.

  6. Julie you are so wise! I’m still married to the man I got married to at the ripe old age of 23. I can’t imagine jumping back into the dating pool but I think these tips are so great! I think often how lucky I am that we grew together (and both of us have changed a ton!) instead of grew apart!

    1. Thank you for your thoughts and I am so happy you are in a wonderful place with your hubs. Sadly, that is not all of our experiences. Certainly not mine. Just keeping it reals. xo

    1. I believe you are right. I do think that life becomes more complicated as we get older and seeing how a perspective new partner handles that can be a Yay or Nay in moving forward. When we are young we don’t have the benefit of life experiences to see how someone will handle those.

  7. Great post! I will be 43 this year, I am remarried now. You are so right, dating in your 20s means time to do whatever you want! But when you have kids, jobs, aging parents, running a household and whatever else comes, it’s a different story. Great advice for those who are ready to love again, I say “ready” because many women think that just because they are single that they are ready. Not true.

    1. So true. Taking the time to figure you out first is most important. Being prepared to date is as important as the dating itself. Good point!

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