Dating : How to date someone decades younger, and make it meaningful for both

After a divorce, I knew I wasn’t ready for another long-term relationship for quite some time, but I really missed a woman. Being alone, with lots of negative feelings like sadness, anger, and guilt; that sucked big time.

I didn’t consider myself proper dating material. Far from it.

Now, the thing is, I’m very good at approaching women. I wrote about my very first steps in that regard, but well, that’s just the tip of the iceberg.

I knew I would approach a woman. I adore women. I totally admit it.

I also knew from experience, that I could easily find women for casual sex.

Problem was though that I don’t like casual sex. Not at all. I want to talk and connect with someone. Laugh together. I long to cuddle. I get horny only after cuddling and connecting for quite some time. I want sex where lust is combined with deeper feelings for that person. And where the sum of those mutual deeper feelings and lust turns into genuine passion while having sex.

But the question for me was, how can I have something meaningful, without ending up with drama and broken hearts.

That is a very serious problem for quite some time after a divorce. There is a big risk that the person you start a relationship with turns out to be a rebound girl or guy. A rebound girl or guy is someone who is only interesting while you are getting over your bad feelings from a previous relationship.

Even couples with very honest intentions from both sides can end up in this situation in a very bad way. This is because the feelings and judgment of the person who is just divorced, are seriously colored by his or her emotional state. Seeing positive emotions in someone else and having a wonderful time feels so great after a period of misery, and is so deeply needed, that someone in that state can easily feel he has found the true love of his life. And things can become very intense very soon. Only, after a period, to find out, that the love isn’t so strong anymore for that person. It was a rebound girl. But the feelings of the rebound-girl were not colored, her love is still there, and she ends up being heart-broken. And if the other is a decent person, he will probably feel very guilty and miserable too.

I learned about this phenomenon from a woman I had a date with very soon after my divorce. We talked about it at length. She said to me, the problem is not that I don’t like you, but that I do like you. But I also know that I cannot trust your feelings for me. And it’s not at all that I don’t want to deal with your feelings of pain to get over your divorce, it’s that I don’t want to deal with my feelings of pain if I completely fall in love with you and you leave me. That risk is too big for me. A relationship is too important for me. I would need at least a year to get over it, probably even more. Then she gave me her number and said, if you’re still single in a year, give me a call. If I’m still single too I’d love to date you. But not now.

I cried that night. Feeling completely miserable. Because of my divorce of course, but also because I thought she had a point. How could I date women like this? So, I felt self-pity. I don’t know a feeling I hate more. But I felt that, very strongly.

When feeling that, that’s when you know, that you need to make a change. I told myself I should fully concentrate on my work, but I failed at that too. I spend time with friends. I could laugh with them, but I still felt completely miserable when I went home. My self-pity didn’t change from it.

I started reading things. That I should learn to value myself. And love myself. But that wasn’t my problem. I already did. I did value myself and knew women did too. I was confident about my ability in my work. I had a great relationship with my kids. And before this period, I also loved spending time being alone. So, I didn’t see a selfesteem problem to work on.

I just wanted to get out of my current emotional state. And I wanted to connect and laugh and cuddle with a woman. It was that simple. Even if it was just one evening a week, with someone I liked, so I had something to look forward too. I knew it would radically change my feelings.

But I also didn’t want something with a high risk of broken-hearts. If that was the only option, I’d rather wait a year, so I could fully trust my feelings and judgment again.

The idea I finally came up with, was to try and find someone with whom I had a great click, but who would be a mismatch for life. That it was clear from the outset, that this was something both valued greatly for a time, but that it would end.

I thought maybe a lesbian curious about a man. Or, someone with tattoos all over her body and an attitude fully outside my comfort zone. Or, someone decades younger. I had just turned 40. Breaking each other’s heart was much more unlikely with those categories I figured. But if they hadn’t found their love of their lives and we had a click, why not try to have a great period together?

I actually went to a bar I knew was popular for lesbians, and approached them to ask their expert opinion about this plan of mine. That didn’t go too well. The first few I approached were rather closed and unwilling to talk with me. Then I talked with a woman who did listen at length, and then thought it was hilarious. Not because she thought I wasn’t sincere, but because she thought I was, and couldn’t believe that I had just come to talk with them about it so openly. She told me she wasn’t curious about sex with a man at all, but approached other women saying things like, you should listen to this guy. This is just too funny. As a result, I spoke with a lot of women. Turned out no one was interested. But I had a great evening. When I left, the woman who had approached other women said to me ‘You are weird, but I like weird. You should come back when you feel bad.’ And then she hugged me.

That night I felt great. God, I loved interacting with women. And that hug, well I loved that too, but wanted way more. But I also felt great, now that I had an idea for action. I could just go out and interact with women again, and talk with them about feelings and relationships. I loved that in itself, but was confident too, that I would find someone with whom I would have a great click and who would be interested in more as well. And for whom the risk of heart-break would be low.

So next I thought students. I didn’t want to go to a bar for that as well, because, I expected, that if they were interested, they probably wanted to keep it discreet. And a bar doesn’t offer that. So I decided to go to a bookstore. Like I had explained in another article, that is a great place to meet and talk with women.

So, after talking with some girls, I met a girl, who didn’t speak Dutch. This was in The Netherlands and that isn’t uncommon at all. I asked her how long she was in The Netherlands and she answered almost two years. After talking with her a bit, it became clear that she intended to stay here, that she had difficulty learning Dutch but thought she should learn it, especially to socialize better. Though people spoke English with her, often they would speak Dutch with each other, and then she couldn’t be part of the conversation. I asked if she had a Dutch boyfriend and she said that no, she was single.

Then I said, I know a great way to learn Dutch. You should go and buy a children’s book here, ages 10 or twelve, and then approach a Dutch guy you like, and ask him to read that together with you. At first, he has to read everything out loud to you and translate the words and sentences. And after he reads you a few sentences he has to repeat the same sentences and see if you still know what it all meant. And then you continue. With lots of repetition. The first half-page might take an hour, but then this will gradually become less because within a story, there is a lot of repetition of the same words.

Once you get better at it, then you read it out loud, and he helps you with the pronunciation. And then move as soon as possible to talk about what you just read in Dutch with each other. That is easier than a random topic because you just read the words you can use when talking. And you do it in a safe environment.

I knew from working at a language institute for foreign students that this is one of the fastest ways to learn a language. Within weeks you can have simple conversations and learning from then on skyrockets because you hear the language all the time and now can follow more and more.

But why would a Dutch guy put in all that time with me?

What is the last time you looked at the mirror? I thought.

I looked around and pointed to some random guy. I said “If he is single and Dutch, I bet a 100 euro, that if you approach him with a children’s book, and you ask him to help you learn Dutch with it, reading it together like I explained, while cuddling naked against each other, that he’ll say yes.”

She laughed.

“But I won’t do that,” she said.

“Why not?”

“He’s not my type.”

“Well, if you approached guys who are your type and asked them, they would say yes. They would say yes even if you said you wanted to have dinner a few times first to see whether you have a click. In a few months, you can have a boyfriend you really like, and speak Dutch.”

“I don’t know,” she said.

Of course, that is to be expected. So many people are completely unwilling to take a chance at approaching others. They keep being alone too long. It’s so tragic.

I’m not that kind of person.

So, I said to this girl, “I would love teaching you Dutch that way, cuddling naked against you.”

She laughed, thinking it was a joke. Then I explained some things about my situation. Looking to get out of my bad feelings. How much I longed to be with someone. And that the chance we would break each other’s hearts would be very small. That we could keep it discreet. That I could teach her a lot. That I could make her laugh. And that we would have a wonderful time together.

She backed out of the conversation. But with a smile.

I don’t feel bad at all when someone says no to me after I have made her laugh. Their no will always be in a very nice way. And I know, that if I approach more women in the same way, it’s easy to find a yes.

So the moment she stepped back I felt great. I had found an approach I had been looking for.

I looked around, but didn’t see any other students at the English section of this bookstore. So I went outside.

I thought, its easy to find out whether someone speaks Dutch or not. I can just ask them a question in Dutch. And that can be anything. And if they don’t know Dutch I can ask where they are from and how long they’ve been here.

So, I went to some busy street and asked girls around twenty, who were alone, if they knew where a specific street was. If they didn’t know Dutch, that was clear right away. Then I would bring the conversation to where they were from and such things. And then to whether they wanted to learn Dutch. And if so, I would tell them what I told the girl in the bookstore.

To make a long story short. I learned a Swedish girl speak Dutch, and then one from Servia as well. Both these girls had felt isolated, but were dynamite and very fun-loving. They were both fantastic young women, with so much going for them. Both smart, very independant and knowledgeable too. Living in a foreign country on your own while not speaking the language takes guts. I genuinely adored them.

Both times we had a wonderful time together. We talked a lot about our feelings, our difficulties, our hopes and our dreams, and also cuddled naked a lot and made passionate love.

And yes, breaking up was easy as well.

I am 100 percent certain, that you can find a wonderful smart student within any western city within a day, with whom you have a great click, and who would say yes to learning a language for a country they want to live. If they are single they often feel isolated and alone. If you make them laugh, and if they feel a click with you, and you offer discretion, why shouldn’t they do it?

No, it isn’t difficult to find someone much younger who is interested. It is about being proactive, about being open, about offering a light-hearted atmosphere, about caring about the feelings the other has, and helping him or her the best you can. If that is your focus, you don’t need to be alone for long. You’ll find a way to talk with others. Okay, I’m skilled, but girls who are decades younger, are a much more difficult category than most others. And you can become skilled too. If you’re single and hate it, stop feeling self-pity and take action.