Six Ways to Make Dating Over 50 Enjoyable

Longing for a partner/By Carolyn Lee Arnold Author of “Fifty first dates after fifty: a memoir”

When we’re looking for a partner in our 50s and beyond, dating can feel like a gloomy slog through the swamp – necessary, but not enjoyable. Yet the longing to find a partner for our later years is real, and if we don’t date, we may never find the person who is right for us. 

Easy to get discouraged

It’s easy to get discouraged and think there is something wrong with us or the men, and then either settle for someone just OK, drop out of dating, or only date when someone matches our list exactly, which is hardly ever.

The right person is out there! What can make dating an enjoyable journey?

It’s part planning and part attitude. At age 57, I wanted a committed partner, so I gave myself the goal of going on 50 first dates with men who were not necessarily my ‘type.’ That goal kept me optimistically moving forward, and I had fun dating a variety of men. After 2.5 years, I found my perfect guy, and we’ve been happily together for 11 years. For details, see the book about my upbeat, sexy dating journey: Fifty first dates after fifty: a memoir”

You don’t have to do exactly what I did. These dating tips and attitudes can be tailored to you!

Six Ways to Make Dating Enjoyable

1. Reframe dating as research 

You are collecting information about who would make the best long-term partner for you. Think outside your type! The qualities that dating apps and first impressions favor – height, weight, age, looks, etc – are not necessarily those that make you happy long-term. 

Focus on what the person is like to be with, how they make you feel, how they treat you and others, and whether you have similar life goals. Be curious about them and you! Do you want to spend more time with them? What are you learning about you? 

The purpose of a first date is to see if you want a second date, and the purpose of a second date is to see if you want to spend more time. Analyze the information you collect, and stay open to someone as long as possible so you don’t miss someone special. 

2. Look for the good in each person 

Look for the best qualities in each person you date, whether or not you want another date. What is special about them? Appreciate them for that. Appreciations are great preparation for being in a relationship. What are they teaching you about what you do or don’t want?

3. Treat dating as practice 

Dating is a skill that takes practice. Dating skills – listening, being curious, looking for the good in people, and not taking things personally—are also great relationship skills. 

Expect to go on a lot of dates to find the person who is right for you. The sooner you start, the better you will become at dating, relating, and finding that special person. One way to develop these skills is through personal growth workshops, which are a fun way to meet people! (See blog post, Ten Ways Relationship Workshops Helped Me Date.) 

4. Create time and motivation for dating

You need in-person dating time, so set aside time each week. Set a goal of a number of dates a week or month. Spend less time swiping, texting, and phoning and get to the in-person dates so you can see what they are like to be with. Find ways to meet people other than on dating apps. (See blog post, Where Did I Find 50 Men to Date?)

Decide what will motivate you to continue dating for the foreseeable future. Is it checking in with a friend, a coach, or a group? For me, it was setting a goal, like a number of dates or a time period, after which I could take a break.  

5. Build in dating support

Expect dating to be a long-term project, so build in a support network of friends, a women’s group, and/or a larger community who will love and support you during your dating journey. Choose people with positive attitudes who will encourage you to keep dating through the ups and downs. (See blog post, 6 Types of Dating Support.)

6. Plan enjoyable dates

Think outside the coffee bar. There are plenty of public, safe things to do outside with a stranger – take a walk, sit in a park, wander around a city, go to a museum or exhibit. Pick a place you enjoy so it is less like an interview and more like a shared experience. And then, appreciate the date and the person!   

Best wishes on your journey!

Carolyn Lee Arnold is a writer, hiker, personal growth workshop assistant, former educational researcher. For more extensive dating tips, see her blog and  learn more about Carolyn Lee Arnold and her tips on dating at fifty + carolynleearnold.com.

Must reads!

Whether you are new to dating, in a relationship but things just don’t feel right or you are making the same mistakes in finding love. The books listed below will help you understand your love sign and what to look for in a partner.

• Attached   – Understanding your attachment style and what to look for in a partner to match you. 
• Fifty first dates after fifty: a memoir-as presented above.
• The 5 Languages of Love, the Secret to Love that Lasts – For singles and couples!
• Finding Love after 50 – From online dating coach Cassie Zampa Keim

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