LILY Letter 116: Developing a Positive Outlook on Dating & Relationships

June 27, 2023

We've heard so many single adults say "I hate dating." Why is that? Perhaps there are as many answers as there are people. But I think they all come down to something deep in our nature that dislikes being judged. And dating gives you more opportunities to be judged than almost anything else. When we pursue a dating relationship with someone we really like, we are always opening ourselves to being judged unworthy, inadequate, or not good enough. And The feeling of being judged that way hurts. It triggers the self-doubts and insecurities we already have.

People may say they don't like dating because they don't like "playing games." But what are the games? The games are the deceptions and ambiguous acts or statements we use to conceal our interest in the attempt to find love without risk. We don't want to "show our hand" before we know how the other person feels, so we joke around, make ambiguous statements to feel the other person out, puzzle it out with our friends, and otherwise fail to be honest about our interest because we are afraid of being judged and rejected. We will do almost any contorted thing to avoid facing rejection directly. 

Knowing what we all fear about dating, what can we do show up better and make dating more joyful? My first suggestion is radical acceptance of the possibility of rejection. That is the price of admission. Remind yourself at the outset that you are taking a risk and that means it may not work out the way you hope. 

Second, recognize that rejection is not about you. Rejection and judgment are about the other person and what they want. The fact that you are not what they want does not mean you are not valuable. They are simply making a choice. Recognize that you are not for everyone, but you are for someone. If someone rejects you, recognize that they are simply not your person--even if you may have really hoped they would be.

Third, cultivate a healthy self image. You are in your middle years now. You have lived a good part of your life. You have likely experienced successes and failures. You know what you like and what you don't like. You have had a chance to develop your strengths. You know the goodness that you are capable of bringing to a relationship. If someone else is unable to see it or appreciate it, you can tell yourself in all confidence that another great person will appreciate you and want what you have to offer. Knowing that makes rejection feel less harsh. 

Finally, remember that dating is simply a matter of getting to know great people. It is exploring the depths of another precious human soul. It is not about games and deceptions and being judged. It is about having fun, making friends, and enjoying new adventures. I will never forget my first date after many years of marriage. I remember getting ready, making sure my clothes and my hair were just right, putting on cologne, and driving to the restaurant with a sense of anticipation. I remember walking in and seeing my date seated at the table. I remember the way her black curls fell around her shoulders and the pleasant smile on her face. We had a couple of hours of pleasant conversation and good food. As I drove home, I was on cloud nine. To be very clear, we didn't decide to become a couple that night. There was no physical affection apart from a hug coming and going (which is customary, at least in Utah, and does not indicate any serious interest). But I felt elated because I was reminded that the company of a beautiful, intelligent, kind, and charming woman is still one of the greatest pleasures in life. I had not experienced that in many years. 

The woman I went on that first date with has remained a good friend. She became one of my best friends. We were never meant to be a couple. But we were in each other's lives for a reason. We supported each other's mid-single journeys and served as wise counselors for each other as we moved forward to rebuild our lives. While that was not the outcome I may have envisioned at the outset, I am grateful that she appeared in my life when she did. She enriched and enhanced my life. 

You may be anywhere from 30 to 70 and feel like you have blown your chance at love. I want to tell you very sincerely that the pleasure of getting to know a special person of the opposite sex is a great adventure and a blessing. Even if you are 65 years old, appreciating the beauty of a full moon while taking a walk at the park or on the beach can feel just as enchanting as it did when you were 25. You are alive and God has placed passions in you for a purpose. Seize the moment. Push past your fear and be bold. It is not too late for you to rediscover joy and be filled with love.


LILY Pod: Make Dating Fun!

LILY Tube: Dating is a Numbers Game

LILY Short: Are Breakups Urgent?

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