Bachelor’s Handbook to Dating in Your 40’s… and Beyond

Dating in your 40s as a man can sound like a moon mission. Bachelors of such a prime age think that finding the love of their lives is close to impossible. As a professional matchmaker, I have met and dealt with several men who feel insecure about their age.

Here’s the big truth that could help you in this dilemma: age is nothing but a number for most women. We now live in a liberal age where most women overlook the year you were born and would rather find a man who could give them a genuine physical, emotional, and mental connection.

If anything, you could use your age to your advantage. You are older but that just means that you are wiser and potentially wealthy in experience. These are factors that should boost your confidence in finding the woman of your dreams.

Entering the dating game in your 40s could be disorienting at first but as your wingman, here are some of my tips that could help you gain a positive outlook on dating in your 40s… or beyond.

Enjoy your time and follow your own pace.

At this rate, you may or may not have received unnecessary comments from people in your life to go out there and widen your circle. It can get overwhelming sometimes which can only ignite the fear of probably ending up alone for the rest of your life.

However, dating, as much as life in general, is not a race. While it may seem that the “age thing” matters, your past situation could also play a big role in your dating game. Maybe you’ve spent most of your time being with someone but it didn’t work out in the end. Perhaps you’ve been through a bad break-up or even a divorce. Or maybe, you’ve found too much comfort on your own, and building yourself as a better man became your top priority. Whatever your past situation is, you are now navigating the dating world as a 40-something-bachelor with no idea what to do.

Dating is not always easy in whatever age group. In your case, it may even seem like a full-time job. You could be meeting people online, joining social and singles groups, or even asking your friends to introduce you to someone. The whole process could take a lot of energy out of you and will drain you if you don’t change your perspective about dating.

Do not dwell on the pressure of finding the right person. Along the way, you will reject people and you will also get rejected from time to time. Just remember to enjoy the company of one another and to have fun in whatever activity you are doing with that person.

Focus on what you can offer and not on what you lack.

It is easy to become critical of yourself. You can be so caught up in your doubts and fears that you’ve lost sight of the things that make you an amazing person… or even a good partner.

Think of the good things that you could put on the table; attributes that make you stand out or even just being a normal decent person. You could be funny, loving, and warm. You could have built a business from scratch. Or, you could be the man who respects women and just wants to make an honest and genuine connection.

Whatever it is, try to shift all of your doubts to all of the great qualities that you could offer. This has always been my go-to advice to men in their 40s who seek my help in meeting someone because it always works. I’ve witnessed a lot of times how a man sheds his fears and doubts about himself and can connect with a woman in the most authentic way.

Set your standards right.

If you are male trying to date in your late 40s, you likely have a clear sense of what you want in a partner. This is probably heavily influenced with past situations and current and future goals. This said, you may also have a whole different set of priorities as well.

While there is an advantage in knowing what you want, you also need to understand that the world has changed. You’ll be navigating a whole new minefield in dating in your 40s. You may even end up being way too serious about the whole dating thing that could scare away your potential partners.

Don’t beat yourself up and let conversations flow in the most natural way. You may “click” or not but the good thing about modern day dating is that you could always try again when it fails.

Love is a great thing and being in a relationship is one of the most amazing experiences a person could have, no matter what your age is. However, it is normal to have self-doubts or even challenges with self-esteem. It would be helpful if you could try and work on yourself first while understanding your wants and needs. The path ahead becomes more simple once you are clear about your objectives and what you want in your relationship at this stage of your life.

Remind yourself that you are still worthy of finding love. It’s not going to be easy, but I can assure you that it is going to be worthwhile.