Guide to Dating for Men in Their 50s

Getting back into the dating game can be tough, especially later in life when the entire dating scene seems to be different than it once was. Where do you start? How do you meet people? Where should you go on dates? How much is too much when indulging information on the first date? When you lay it all out like that, dating seems daunting, but it doesn’t have to be. Listed below is a guide to dating for men in their 50s: everything you need to know and more to be successful when looking for love again.

Meet Someone Through a Trusted Source

First things first, dating online is not always all that it is cracked up to be. We get it, you can sign up for a million dating apps and scroll through a million profiles until you can’t feel the tips of your fingers, but will it really get you anywhere? It may get you dates, but will it find you love? As you start dating again later in life, you have to remember that it shouldn’t be about how many dates you get, but rather the quality of dates you get.

In your older years, you are more secure with who you are and what you want out of life and a partner. We believe that these love connections are most often found through set-ups. It can be through friends or co-workers, or personal matchmaking services where the matchmaker actually takes the time to get to know you on a personal level, rather than a computer algorithm telling you who your perfect match is. We believe that meeting someone through a trusted source will give you better chances at finding true love.

Patience is a Virtue 

One of the most important things to remember when starting to date again in your 50s is to be patient. Love is not going to happen overnight, and the dating game is different than it used to be which means you need to allow yourself an adjustment period. Let’s be honest, if you haven’t been on a date in 30 years, your first one may not go how you originally imagined, and that’s okay! Be patient as you ease back into the dating scene. Whether you met someone through a dating service, through a mutual friend, or at your weekly bowling league, just remember to take it slow and be yourself.

Be Active and Adventurous

The thing about dating in your 50s, is that most of the time this is your second or maybe third go at love and most likely the same goes for any potential partner you have. Whether you are a divorcee or a widow, getting that push to find love a second time probably didn’t come easy. Stepping out of your comfort zone should be your new motto because when you start to date again, you must be adventurous and active with your new love interest. Marriages and relationships often fail because partners stop being adventurous. Find fun activities for you and your date to do like jet-skiing, going to the beach, wine tasting, music in the park, a painting or ceramics class. The options are endless, the challenging part is not getting stuck in a rut and forgetting how important it is to continuously try new things and be active in your relationship endeavours!

Listen to your Date

It sounds simple, it seems easy, yet so often we forget to simply listen to others rather than talk about ourselves. It is important to be engaged in the conversation, know when it is your time to speak and when it is your time to listen. Females dating again in their 40s or 50s may have spent years not being heard, they want to know that as a potential new partner, you really hear what they are saying and engage with it. The better listener you are, the better the conversation will flow naturally.

Transparency is Key

We asked the question earlier, “How much is too much?” Being transparent in a new relationship is important but knowing when to divulge information is also important. Harping on a past relationship during a first date is a no-no. There is being honest, and being too honest, and finding the balance between the two is crucial when you are just starting to date again. You definitely need to be transparent in terms of what you are looking for in a partner, expectations, end-goal (marriage, long-term committed relationship, casual dating), whatever it is that you want, be honest about it so that you and your date have the opportunity to see if your personalities and expectations align. As you get to know each other more, continue to be transparent, this way nothing will ever come as a (bad) surprise to your partner.

Date the Right Aged Person 

Often men in their 50s who are exploring the dating world again have unrealistic ideas of dating younger women. Although this may be ideal, it is not realistic the majority of the time. When you use a personal dating service or are set up with someone via friend or co-worker you will most likely be set up with someone in your age range, let’s say within 5 years of your own age. A 50 year old male with a 35 year old female is likely to not have a long lasting relationship because they simply are not in the same place in their lives. AGAIN, this is not ALWAYS the case, but more likely than not, dating someone in the same age range as you will likely stand a better chance of success.

As you grow older, you become more self-aware of what you want out of life and often the things you searched for in your 30s have come and gone, such as financial success and stability or having children; now in your 50s you may want to travel more or enjoy retirement, money may not be a daily worry like it was in your younger years. These simple things have to be thought about and considered when you start to think about dating someone much younger. By dating someone within your age range, you won’t have to worry so much about you being in separate places in your life, instead you can find common ground and enjoy activities and a lifestyle fit for you both.

Guide to Dating for Men in Their 50s

Now that you have read through our guide to dating for men in their 50s, you should have a solid understanding of what it takes to successfully date as you grow older. When searching for love a second or third time, it is important to remember to be honest and let your expectations be known. You don’t want your time wasted, just as a female in her 50s doesn’t want her time wasted as well. If you are just entering the dating scene again, remember to be adventurous and try new things. Keep things interesting so that your love has an opportunity to prosper!

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