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Dating in your forties

 When you are younger and in your 20s dating has an optimistic ring to it (Photo: Courtesy)

Dating is hard! I do not know if there is anyone who enjoys dating especially the first few dates - it is awkward, pretentious, and cringe-worthy.

When you are younger and in your 20s dating has an optimistic ring to it because you still have the twinkle in your eye and believe that love can conquer all because you still believe in fairy tales.

Nevertheless, when you are older you sometimes can be a little jaded or quickly come to realise that life is not really black and white. The realisation that everyone comes into relationships with baggage you included, can be quite enlightening.

Also, you realise that relationships look nothing like the Hollywood or Telenova ideals you spent your younger year devouring and believing as the gospel truth. Instead, they require work, sacrifice, commitment, and forgiveness.

Nonetheless, this does not mean that dating when you are older can't be even more wonderful than it was in your 20s. This is because as you get older you become wiser, have realistic expectations, and are clear about what you want and do not want.

It is worth noting that the idea of dating while older was not a reality in our parents' days, but it is becoming more of a reality for many. On the dating scene, apart from widows and widowers, we now have single people who have never been married before. There is also a big number of divorcees as divorce and separation increase.

So, even though our mothers and fathers did not have to worry about dating when older, we have to.


Kalekye Mumo, a media professional, actress, and influencer in her 40s, says the dating game plays out a little different as you get older and it is important to know how to navigate it.

"To begin with, we need to remember that dating is the process of gathering data about the other person in order to understand the other person's values and find out if they align with values," says Kalekye.

"So, I would advise anyone getting into dating after their mid-30s to first ensure that they know who they are and what they stand for in order to know what they want and be able to voice it. Also, the older you get you to learn that no one person can give you all 100 per cent of what you are looking for.

"Instead of looking for someone to complete you, understand that you are already complete as you are and focus on looking for someone who complements you and vice versa," she says.

She says that it is important to understand that the older you get the more baggage you will have collected along the way, so one should get into dating with an open mind and extend some grace to the other person.

"This makes it easier to see what you can live with and what you can't and then whether to continue dating or set the person free. For example, there is a high chance that even if a man is single, he may have a child or children.

"So, if you are dating said man, you've decided that you can live with this baggage and you should both be clear about the roles you will play in the child or children's life and you must also be prepared for the response the child will have toward you. You should also go in with the understanding that the child has a mother who will be present to co-parent so you will both have to figure out the healthy boundaries," explains Kalekye.

Further, she continues, that the biggest challenge of dating when you are in your late 30s and 40s, is that opportunities to meet potential single available partners with similar values are less.

"There are barely any platforms to meet mature men who are looking to settle down. It is even more difficult if you are looking for a man that is not only available but also saved," she says.

Most eligible men who are born again are either taken or shying away from the church because of a failed marriage.

"Away from the church you get a lot of men in this age group who are single but not ever ready to settle, or is they are divorced or separated they most just want to have fun and date girls in their 20s who will not stress them with grown up questions that require them to think hard or take responsibility," she explains.

Kalekye says the lack of social mixers and platforms for older single and available partners is a big hurdle to dating.

"If you are born again, it is even harder because you don't go out clubbing and to tell you the truth very few churches remember to cater to those who are older and looking for love or even extend grace to those who may have married wrong and divorced.

"The only all-inclusive event for this group of people that I heard about was held by Parklands Baptist sometime this past July. It was specifically designed to cater to older singles who had never married, widows, widowers, and for those who are separated and divorced. I found the event so exclusive and spot on," she says.

In addition, if you find yourself dating when you are older, allow yourself to evolve.

"Also allow yourself to evolve don't be so set and stuck in your past beliefs that you miss out on a good partner. Not everything that was important to me in my 20s is still important anymore.

"For example, when I was younger the idea of settling for a guy who had had a child would not work for me, but now I think I am quite open to it because it takes away the pressure in event that I am not blessed with a child."

Lastly, Kalekye advises that those who are looking to find love in their later ages should continue living their truth and being open to meeting someone who may not fulfil all that they are looking for. Be open, be proactive and ask friends and family to introduce you to potential partners.


Eve D'Souza, 43, an actress and business owner, says that she found dating in her late 30s to be difficult.

"It was so frustrating. I can honestly say my 30s were my most difficult years when it came to dating! To begin with, you have to deal with all the emotional baggage. At this age you meet both men and women who have been through it all, painful breakups, traumatic experiences, trust issues, disillusionment and so much more," she says.

"There were also limited options. My single girlfriends and I often complained we rarely met anyone new that we could date. It was so difficult to meet available men, the dating pool in Nairobi for people in their 30s was small and I mostly met men I didn't connect with or ones who were not looking for a serious relationship. I must admit, I don't think I was ready either, I hadn't dealt with my own issues or started my healing process."

Eve, says that at this age one needs to be careful because not everyone is looking for the same thing in the older dating scene.

"In your 30s there are options of men who would like to date around and only have fun, mostly because they have been through a difficult breakup and are still processing it. There are also quite a few men with children from a previous relationship and I don't think dating is easy for them either.

"You will read lots of articles warning women about dating a man with children but there is hardly any positive advice or support for men or even women who have kids and are dating again which is unfortunate because they too should be able to find love," says Eve.

She says everything changed for her at the start of 2018 when she gave up on love and accepted that she was meant to be single for the rest of her life.

"I remember letting go of the idea of being married. I let go of unhealthy patterns and connections. I had decided I would not put any pressure on myself to get married but for some reason, I also made more of an effort to meet new people and step out of my comfort zone. I met my husband exactly one month later!"

Eve says she met her husband when she was 39 and he was 41.

"It may have been a case of the right timing for both of us but my experience with Simon was like no other, I grew a lot on a personal and emotional level. Our relationship helped me heal many wounds but also forced me to take positive steps toward much-needed change. Because he was so loving and protective, I felt safe enough to step out of my comfort zone and build better relationship habits.

"It was a little scary after so many years of being single and independent to start creating space in my life for someone else. I realised in the process that I didn't actually know how to have a healthy relationship but I wanted better for myself."

However, Eve says getting married later ended up working for her because being single forced her to deal with her wounds.

"I learnt that I had very little self-awareness and had not been taking necessary steps to heal. That I was sabotaging my own happiness most of the time by deliberately picking partners that I didn't even see a future with.

"I went through a period of creating only unhealthy attachments because I was not willing to address all the uncomfortable feelings I had held inside for years. I had feelings of fear, shame, and loneliness, due to a very painful life experience I didn't want to address."

In closing she advices: "We all seek companionship, and it is truly a beautiful thing, but don't rush into serious relationships or commit for the wrong reasons. There is no deadline to finding love. Stop putting so much pressure on yourself to find someone, you will make choices from a place of fear. However, do step out of your comfort zone and put yourself out there and keep an open mind and most of all enjoy the process."

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