Dating in midlife is a scary proposition for most of us. Maybe it’s been decades since you got naked in front of someone new other than a doctor, or nobody but your ex has seen your stretch marks or smelled your morning breath since college. You might be worried about the rules of game, like who makes the first contact? How do you decide who pays for a date?  And what does it mean if you let someone buy you dinner? How do you decide who is a good candidate after the miserable fail of the last relationship?

I am a relationship expert and I had major butterflies as I began to date after my divorce. Here are five things I figured out that helped me.

1.  FIX THE PROBLEMS FIRST

If your car breaks down, you take it to a mechanic and get it fixed before you take it out on a road trip, right?  Fixing yourself is not that different. You probably have accumulated a lot of baggage, bad habits and unconscious coping patterns that need to be addressed. DIvorce is an opportunity to learn from your past mistakes.  If you married young you may not have developed your own identity fully or understood what you wanted and needed in a partner. This is where your age becomes an advantage. Dating in your 40s or 50s you are more likely to know yourself and to choose a partner that compliments your lifestyle and values. 

Take the time to learn to have compassion for yourself so you will attract people who are healthy and you will quickly recognize unhealthy behaviors in a potential partner and move along. Being alone is better than being lonely in a relationship.  As a couples therapist, I have seen a lot of examples of marriages over the years. With my divorce, I had a lot of baggage to unpack, including figuring out how I could have ignored major issues that were right in front of me.  I spent a lot of time in therapy, in groups, and reading everything I could get my hands on while I unraveled the mess. If you do your healing, you will be less likely to repeat your mistakes.

2.   IT IS SUPPOSED TO BE FUN

After a year of healing my heart after my divorce, I decided I was ready to take my friends’ advice and get back into dating.  The anxiety was intense. I didn’t know the rules and knew I was out of practice. I decided I was taking it too seriously in thinking I was looking for another partner and I should just get out and “practice” dating and make friends.  This felt a lot more manageable. Don’t listen to the fear, just move forward and see what happens. It doesn’t have to be perfect. Thinking of it as ‘fun’ may help.

3. DO SOME HOMEWORK IN PREPARATION

Take some time and make a list of qualities your ideal relationship would include along with a list of non-starters.   This will help you weed through the dating profiles quickly and save time and energy. My ideal partner had high emotional intelligence—able to name their feelings and work through any issues with a fair amount of skill.  They must have a number of rich intimate relationships with family or long term friends and children of their own.  Nonstarters were addiction issues, problems managing money, and narcissistic traits.

In addition to designing your perfect mate, you might want to ask friends and family that have dated in the last decade to share some rules of the road.  How did they decide who to go out with? Who pays for a date? What are the current expectations for intimacy and how did they deal with that? Most importantly, what do you feel comfortable with?  From a relationship expert, let me tell you that if you can’t talk about sex with someone, you aren’t ready to have that kind of intimacy with them.

You also will want to be prepared to protect yourself against STDs if you plan to be sexually active. See your doctor and be prepared.

4. PICK YOUR ROUTE

Once your “ideal mate” list is complete, it’s time to think about where you will find your potential dates. My preference would have been to meet someone through a friend or in a setting that was more about a shared interest.  I had thoughts that my ideal man would show himself in the Market of Choice produce department talking about the best way to prepare butternut squash.  I spent a lot of time and money in that grocery store but no dates materialized.  As a therapist, I’m not going to meet people to date at work and most of my friends are married.  Single men were not easy to come by in my environment, so I decided to sign up for online dating. 

We have all heard horror stories about online dating.  Some of them are true.  People from all walks of life put their best selves out there and are looking for love…or a hookup. You are left to figure out which. Over a period of a few weeks I read about 400 profiles and narrowed it down to maybe 10 that were of interest.  It’s a lot of work, but I felt pretty confident that most of these people, provided they were honest in their correspondence, were potential partner material.  

If you don’t like the idea of online dating, consider signing up for a meetup group doing an activity you enjoy.  Put the word out to your friends that you are interested in dating and would like to be set up.  Or find someone that is single in one of your regular haunts like the gym, church or a volunteer organization.  

4.    TAKE IT SLOWLY

There’s no fire to put out.  You don’t suddenly become an unattractive potential partner at your next birthday.  Remember, being alone is much better than being lonely-choosing a partner that is wrong for you will cost you time. 

My plan included exchanging messages with some of these men I found online, making sure that my list of must-haves was as complete as I could tell without meeting them face to face.  One in particular was interesting and we agreed to meet somewhere for dinner. We had a nice evening, including a walk along a pier on a beautiful summer night and lickety-split I was in a relationship for 6 months.  Until I figured out that I had missed a few red flags. Oops. That was not taking it slow.  What had I overlooked and why was I missing those signs?   I revised my dating prerequisites, examined my own baggage and went at it again.

The next round was much more fruitful.  I decided to keep the dates short, including only a drink or lunch rather than the formal meal of dinner so I could escape quickly and easily if they were not what I was interested in.   I went on quite a few first dates and met some very nice men.  By the end of the first date, I could often scope out serious relationship material or decide if we could be friends.  One, in particular, drew my attention because he had a funny list of things he was good at in his profile including holding very still at the dentist’s office.  That humility was high on my list of dating attributes.

5.  BE TRANSPARENT

Put it all out there. “Intimacy is the capacity to be rather weird with someone — and finding that that’s ok with them” says Alain de Botton.  If we all entered relationships with it all hanging out, we have no phase of idealizing someone and then being disappointed by their faults.  Share the ways in which you know you are flawed, what challenged you in your last marriage and what you have learned from your life experience.  If someone is turned off by the ways you are weird, better to know that now than later.  Move on and find someone that will love you for who you are.

Six and a half years later, I’m married to the dentists’ dream guy.  Did I get lucky? Yes!  But I also think that my dating approach had something to do with it.  I took the time to know myself and what I wanted.  I understood what I had to offer.  I had fun meeting people and picked up some great stories along the way.  Dating after divorce took a little courage, a lot of willingness to sort through the profiles for a hidden gem, and the willingness to try. 

It was worth it.

Her e-course, Stagger, Stumble and Stand is chock-full of tips about how to heal your heart after a break up. It comes with hours of entertaining video instruction, pdfs, and meditations. If you are interested in individual or group coaching, contact her. She has a new women’s divorce coaching groups starting soon. Maybe focus on healing your childhood issues and beginning to date? You don’t need to do this alone.

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