Would you date an older man or woman?

20somethingPursuit[notice]Revivalist Shannon-Leigh Barry shares her wit and passion and the pursuits of her 20something heart in a monthly column that speaks to the desires of young adults in today’s Christian society. [/notice]

I’ve just arrived back in South Africa from some time overseas. On my arrival conversations have now shifted between my friends from weddings, to proposals and dating older men. My best friend is getting married and so my journey begins with becoming the most accommodating bridesmaid. She is blissfully happy and comfortable with her soon to be husband. She is closing out her twenties while he is in his early forties. The age dynamic seems to work for both of them. I have to ask myself is age nothing but a number?

The pursuit of an older man
About two years ago I met an older man through a mutual friend. I wouldn’t say he was my type. If he asked me out just mere face to face I would have probably told him I wasn’t interested. I remember the first day meeting him. He was so intrigued by me; he asked so many questions: What I liked to do, where I liked to eat out, etc. Of course, I should have known he was in hospitality — I didn’t know for a while, which made this slightly more interesting. After speaking to me for the first time the button of pursuit was switched on because when I got to work the next day there was a flower delivery of my favourite flowers: tall long stemmed Texan roses. The kind that you can actually hold without getting your hands hurt. I thought it was for the office until I saw a card that read. “Shannon, I really enjoyed our conversation”. I knew he is going to ask me out for a dinner soon, because that always accompanies flowers. Well, in the movies you know it does. Part of me was thinking “what are you doing, this man has got to be more than ten years older than you! It could even be 15!” It’s not like I was going to be asking age appropriate questions. So I agreed to a lunch date; nothing too special with the intention of communicating that we don’t have much in common.

Lunch goes well. I get to ask all my questions. Are you Christian? Have you been married before? And other questions that only a younger person would have floating in their mind. To people watching us I probably looked like a gold digger and he looked like a man having a mid-life crisis. He was charming nonetheless and before I knew it I was being drawn in.

So I thought it was best to stick to coffee dates. I wanted to get to know him and also didn’t want to blow him off because of his age. The conversations were so different from what you would discuss with a man in his twenties and he was surprised at the wit of my twenty something mind. So as long as we are both enjoying the conversation and there’s respect, let’s see where this goes.

The surprises kept coming. From picnics in the parks in front of musicians, to dinners in beautiful places… food was a love language we were going to enjoy together. I realised that one advantage of dating an older man was that he had the art of pursuit down, not like a younger male who would have had a panic attack just packing a picnic basket for our date. True story. An older man knows how to perceive what you would need only because he has had more training in understanding women and romance.

I really enjoyed meeting him and spending time with him. The conversations were memorable and the pursuit alluring. The challenge we faced was that his career was seen as more important than what I was doing. We were in completely different seasons of what we were wanting for ourselves. That became a deal breaker for me. I still wanted to explore my career and travel and he was looking for someone to fit into his world… a world that was already established before meeting me. Being honest with myself meant saying “thanks but no thanks!”

If you are a younger male pursuing an older woman the one thing that you might face is a list of expectations. Maturity and emotions could be a challenge but I have seen couples do relationships well even though the woman is older. Younger could mean more attentive and more open to exploring. Friendships circles could make for interesting nights out with your friends all slightly jealous of your experience.

It could be slightly different for you and you could really make things work like my best friend and other friends of mine.

Here are some Questions you should ask yourself if you are considering dating older:

What does baggage look like?
You are going to have to understand that dating older might come with some attachments like an ex-wife or children. To fully love and accept this person means you have to take everything that comes with this person. In some cases there might be some drama attached that will take time to work out. You have to be committed to sticking through those times until they smooth out.

Are they having a midlife crisis?
We have all seen this one: the older man in his sports car with the younger woman in the passenger seat. There’s nothing wrong with liking a grey haired Richard Gere looking man or even dating a cougar/panther (older woman, as we say) as long as you aren’t the handbag: the item on their arm that represents a fountain of youth to be displayed around. Is what you have genuine?

Do you want many kids?
The chance of a person in their forties or later wanting to have three kids is highly unlikely. Big families need time and attention and probably buckets full of energy. Expecting a man or woman to have children at that stage of their lives is asking a lot. Asking a forty year old for a child means they will be seventy when the baby is thirty. That estimation is quite realistic isn’t it. So expectations on the big family you desired might need to be adjusted.

Are your career paths very different?
If you are starting to find your feet in your career or even consider changing careers in your twenties and thirties, this is probably the most flexible time to explore what you want to do in the future. Many of us travel to different cities in hope for better prospects and quite frankly only have to think of ourselves in the process. Dating someone older could mean that they are more established in their careers and might not want to take all the risks you are willing too. They could view their occupations as more serious and yours not as important because you are still young. This is something you would have to talk through, especially if you are ambitious. I would say this one is a deal breaker for most.

Do you enjoy the conversation?
Depending on how big the age gap, you might want to talk about different things which could determine whether that person stays engaged as you discuss your last blog or job prospect. Meaning: Do they genuinely care, regardless of whether they even like your social media updates or what the future holds. It is also important that you are the same person with your friends and family as when you are in their company. No need to act more mature than you are. That comes with time.

Love is different for everyone and all of us have different needs.
You shouldn’t exclude someone just because they are older. Or, you could be the older person reading this and disqualifying yourself. Remember that relationships are not about comparison.They are real and a place where we should be able to take risks as well.

So with that said, what I have learnt most is: There is no set formula for love.


  1. Great insight Shannon! You take a very mature, grounded look at this topic, and your points are right on.

    There are SO MANY advantages to dating someone even a few years older, particularly on a practical level. That being said, for me personally, I love the idea of growing up with someone – starting things off before either of us have come into our own. That can come with a lot of frustrations, but there’s something beautiful intimate about it as well.

  2. I was reading this in your voice, lol, I miss our Italy con-van-sations :-) Good job, get it girl!