Dating can be fun regardless of your age. But when I look back on dating when I was in my twenties compared to dating now when I’m 41, there are some major differences.
These differences come from many things. Some of it is simply being older. With experience comes wisdom, as they say, and that wisdom puts a different color on dating.
But it can also be because of lessons you’ve learned from being married and then divorced. It can be because your perspective on what you want from a relationship, or whether you even want a relationship at all, has changed.
So what are the differences I’ve noticed? There are a lot of them and they’re not all bad.
I’m more comfortable declining a date
Whether it’s a guy asking me out for the first time or one hoping for a second or third date, I am much more comfortable declining now that I’m older.
When I was in my twenties, saying no to a date felt rude. Even if I didn’t like the guy, it felt like I was being mean to turn him down for a date.
On top of that, I didn’t really know yet what I wanted from a relationship or a partner. So I was open to dating pretty much anyone because I figured anyone could be “the one.”
In my 40s, I know what I want from a relationship and a partner. And if I know a man doesn’t match up, I decline. If I’m not feeling it, whether it’s a lack of physical attraction or something else, I decline. And I feel no guilt.
In fact, the way I see it, I’m doing us both a favor. Why should either of us waste our time if one of us isn’t truly interested?
My kids are always part of the picture
My kids are older. I have a 19-year-old who still lives at home and a 16-year-old. They’ll both soon be on their own, but they’ll always be a big part of my life. So while I may not be looking for someone who would be the kind of stepfather who they could call Dad (because at this point, I’m sure they wouldn’t), I am still looking for someone who will understand that my kids are always going to be important.
I don’t introduce men I date to my kids unless and until it gets serious, but it still matters to me that any man I go out with knows I have kids and isn’t just willing to tolerate that but is happy about it. It matters to me that he is willing to become part of a family, even if that family isn’t all living in the same house and raising kids together.
I only date other parents — and what stage they’re in matters
I learned very quickly that dating other single parents is probably the best option. Only other parents truly understand having to bail mid-date because your kid has separation anxiety or canceling a date completely because of a sick kid or a babysitter who flaked (or got grounded).
But what stage of parenting they’re in matters. Now that my kids are grown or nearly grown, I have less interest in starting over, even if my role would only be as a stepmother who helps out. But I’ve also noticed that, regardless of their own age, men who have younger children often seem to want to leave the door open to having more — and I’ve not only closed and locked that door but also thrown away the key.
I’ve been asked why, if my kids are older, dating another parent still matters so much. The reason is fairly simple: in my experience, men who are my age or within the age range I’d date at this point who don’t have children don’t want them — even as stepchildren. They have no interest in being part of a family where they’d be around my adult children and any future grandchildren my kids might give me, spending holidays together or visiting on vacations or having Sunday dinners together.
And I don’t want my partner and my children to be two separate parts of my life.
Men are eager to trash talk their ex
Let me begin this section with a disclaimer: I’m sure we women are just as guilty of this as men. However, I don’t date women, so I can’t speak to that experience personally.
I am absolutely amazed at how many men have completely trashed their ex to me on a first date. I’ve heard many men talk about the mother of their children by referring to her as a bitch, a whore, a cunt, a gold digger. They tell me they hate her, can’t stand her, or they wish she’d die or fall off the face of the planet.
I understand that there can be animosity toward an ex. I’ve been there. But when you’re talking about the mother of your child like this, it brings two thoughts to mind for me. One is to feel bad for your kids because even if you don’t express these thoughts to them, they probably sense them and it must be so painful for them.
The other thought is to wonder if this is what you’d say about me if this date works out and we have a relationship and then break up. If you can talk this way about the woman who bore your children, you might say far worse about me.
This was not something that happened when I dated in my twenties, probably because at that age, most of us don’t have the lengthy and often complicated relationship history we do in our forties.
But for the record, men and women alike: no matter how difficult your relationship with your ex, save the trash talking for after you get to know someone. It leaves a really negative first impression to someone you’ve only just started dating.
I take things much more slowly
When I was dating in my twenties, I felt a strong sense of urgency. I honestly have no idea why. I just felt like I needed to get things moving fast so I could find my forever and get started on it. And of course, that ended in a divorce after a short-lived marriage that my ex-husband and I entered way too quickly.
Now in my 40s, I don’t rush anything. I’d rather take my time and get to know someone thoroughly before I make a decision about a potential future together. I’d rather go slowly so if the red flags start popping up, I have time to put the brakes on and get out before I’m in so deep that I can’t get out.
I also take it slow now to make sure sex doesn’t cloud anyone’s judgment. Sex can be great but it can also make it far too easy for one or both people to start thinking there’s something more between us than there really is. By keeping it off the table until we’ve gotten a better feel for how we vibe in other ways, I can be sure that whatever feelings I might have for someone are real and not just lust and a desire for another orgasm being confused with love.
Men don’t seem to put as much effort in
I’m not sure if this is truly the result of dating men who are also older or if it’s just that things have changed since I was dating in my twenties, but I notice that many of the men I date don’t put as much effort in as the men I dated in my twenties.
When I was younger, the men I dated would dress up for a date. It might still be jeans and a t-shirt, but they’d be clean, unwrinkled, and the guy smelled good. I’ve gone out with several men in more recent times who came looking like they’d just finished weeding a garden, herding cattle, or straight from the gym sans shower.
But it’s more than the way they dress. They seem bored with the conversation. Their answers to questions I ask sound stilted. They ask questions as if they feel forced rather than being actually interested in getting to know me. They don’t even take the time to walk me to my car.
They don’t plan dates in advance. They want to call at the last minute and go out right now. When they do that, they don’t have an idea in mind for what we’ll do. Or they want me to come up with something. It’s all very frustrating.
Of course, you might argue that I’m just choosing jerks to date. But some of these men have been guys friends have set me up with, raving about how great they are.
I’m not sure where the lack of effort comes from or why but I do know that it’s a huge turn off. It’s a big reason why there are many first dates and not as many second dates.
I am both more open-minded and pickier
When I dated in my twenties, I had a goal: I wanted to get married and have kids. I dated with that as my sole focus. If a man wanted that too, that was enough reason to date him, even if I wasn’t really interested. I would tell myself that I needed to get to know him better before I could decide I did or didn’t like him.
Now that I’m in my forties, I’m much more open-minded about my reason for dating. If the right guy came along, I’d be open to getting married again, but it’s not my goal. My goal now is to have fun, meet some nice guys, and eventually perhaps find someone to share my life with, married or not.
But I’m also a lot choosier about who I date. If there’s zero physical attraction, I don’t date the guy at all. Physical attraction isn’t everything but it matters. And there are a few key areas where we need to have similar views and interests. If we don’t, he’s crossed off the list. I’m less willing to budge on what I’m looking for in a partner.
I put myself first
When I was in my twenties, I would drop everything for a guy. Call me at the last minute for a date? Sure, no problem! Cheated on me? That’s okay, I can forgive it! Want me to wear different clothes or a different hairstyle or get a different job? Not an issue!
But now? I come first. I know myself deeply and fully. I know what I like, what I want, and what matters to me. And I won’t compromise nor will I let a partner think he can change or control me.
I’ll hear a date out on what he wants and needs in a partner or relationship, but if our wants and needs are different and there’s no room to compromise, I’ll walk away instead of trying to conform to what he wants or needs.
And if I find a red flag on the first date? I walk.
I don’t expect him to make me his first priority when it’s a first date or we haven’t been dating long at all. But I do expect to be important enough for him to plan ahead for a date, to show up on time or offer a clear and honest explanation when he’s late or cancels, to pay more attention to me than his phone, and to call or text when he says he will. If he can’t do that, then I need to value myself enough to walk away and wait for someone who will.
Dating in my 40s is better
Despite some of the drawbacks I mentioned above, I think dating in my forties is better. I’m more confident and comfortable. I worry less about whether my date likes me and more about whether I like him. I don’t take rejection as personally.
I know what I want and I allow myself to decide someone isn’t a good match without feeling guilty or wondering if I should change what I want.
So whether it’s a great date or one that clearly isn’t going to lead to another, I consider each date to be successful merely because I can identify which category it falls into — something I didn’t always do when I was in my twenties.
Maybe the best part of dating in my forties is that it’s a choice. In my twenties, I felt like I had to date. I was young and single and that meant dating was required. But now that I’m in my forties, I know it’s a choice. And it’s a choice I make frequently. Sometimes I take a break because I’d rather enjoy my own company or I’ve had a string of bad dates and just need a breather.
And sometimes I take a break because there’s a pandemic and virtual dates just aren’t the same thing.
But it’s still my choice.
Wendy Miller is a Certified Happiness Coach, freelance writer & meditation teacher. After years of settling for abusive and otherwise toxic relationships, she got fed up. Using meditation and other tools, she got to work on healing herself, setting boundaries, and only engaging in relationships (romantic and otherwise) that bring her joy. She wants to help other single parents find the love & happiness they seek, including and going beyond romantic love. She lives in Florida with her two sons, where she homeschools while solo parenting, while surrounded by what feels like a zooful of animals.
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