S1.Ep12: Dating again at 40

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This week’s caller is Ashley, who just turned 40. Ashley recently got back into the dating game, and she’s feeling insecure about her age. She doesn’t necessarily “look 40,” but she’s got some hang-ups about what it means for her in the dating world. She knows it’s blocking her from finding her person and called into the hotline for some perspective.

Whether you’re a woman over 40 or not, you too have been fed messages about how aging isn’t okay and you might resonate with the immense pressure of looking a certain way, especially if you’re dating. Ashley knows this thought is blocking her from putting herself out there, and I’m offering her some alternative thoughts.

Tune in this week to hear Ashley’s thoughts about why she feels she has to settle for dating people who are 40 or above. We’re discussing how Ashley is rejecting herself before anyone else can, why we do this to ourselves, and the power of practicing self-compassion when our brains offer us safety over what we really want. 

If you want to call in to The Life Coach Hotline, go to lindseymango coaching.com/lifecoachhotline.

What You'll Learn on this Episode

  • The fear and discomfort Ashley is experiencing about getting back into dating. 
  • Why Ashley believes she has to settle for older people to date.
  • How our brains trick us into choosing safety over what we really want. 
  • The thoughts Ashley has about being interested in younger guys. 
  • How self-compassion is the secret to moving forward. 

Featured on the Show


Click to Read Episode Transcript

Lindsey: Hi, welcome to The Life Coach Hotline. This is Lindsey Mango, your life coach. How can I help you?

Ashley: Hi, Lindsey, this is Ashley. I have a couple of things that I wanted to try to work out and I recently turned 40. I never thought I would care about that, I have an older sister who cares every year after 40 and I get it now.

Lindsey: Yeah.

Ashley: And so I recently got back in the dating game and I feel like I don’t necessarily look 40, but when you get down to it there are definitely things that happen as you age. And I’m feeling a little insecure out in the dating world because I might not look 40 but there’s wrinkles, there’s things that are not as tight anymore and I feel like I have to date 40 and above. I feel like the younger guys are out of the question.

And I may find somebody who is older and that’s perfect. But I just find myself seeking out people who I think are older than me because they’re not as tight and wrinkly, you know what I mean? And it’s like, what if my guy is a little younger than me?

Lindsey: Yeah.

Ashley: And I’m not even opening myself up to that.

Lindsey: Yeah, it’s almost like you feel safer dating the older guys it sounds like because then you’re like, well, at least I know that they’re going to be –

Ashley: Saggy as well.

Lindsey: Yes. Okay, so let’s start here, do you have a niece or anything? I know you have kids.

Ashley: Yeah, I have two nieces, two little girls. Yeah.

Lindsey: Okay. So I want you to imagine if they came to you and they were in their 40s and they had the same fear or discomfort. What would it look like for you to offer them some compassion and love if this is what they brought to the table?

Ashley: Yeah, I mean, I would never tell them, “Oh yeah, find someone who is old and saggy.” I would tell them that they have so much to offer. That they’re beautiful just the way they are. That their person, whoever that person is, is going to love every wrinkle or not even notice it, not even care. I would just tell them all those things that it’s so hard to tell myself because, of course, I would never say any of the things that I say to myself to my children, to my nieces, to my friends.

Why is it so hard to be able to tell yourself those things and really believe them?

Lindsey: Well, I think you’re in your own brain, right? And your brain wants to protect you, and so think about it like this, you’re trying to rip out the rug from under you before anyone else can. So you’re critical of yourself because then if somebody is critical of you, you’re like well at least I already knew that or at least I already prepared myself for that, rather than the discomfort.

Think about it like this, if you really put yourself out there and just owned everything that you brought to the table, what are you afraid would potentially happen?

Ashley: That I would get rejected. That someone would say, “Oh, you’re too old.”

Lindsey: Yeah.

Ashley: Let’s just say that that is the worst-case scenario, “Oh, no, you’re way too old for me.” And it’s like, okay, so like talking to you it’s like, okay, that doesn’t make me less than. Let’s find someone who doesn’t think I’m too old. It really should be that simple. Or maybe I’m just not that person’s type, and that’s okay. That doesn’t make me less than. There are plenty of other people. My friends have husbands who I don’t think are – You know what I mean?

Lindsey: Yeah.

Ashley: It doesn’t mean anything about me personally. It’s just where is that block? Where is there, how come I can’t get past it?

Lindsey: Well, I think the biggest thing is you’re making it a problem, instead of seeing this as your humanness. Of course your brain is telling you this. Even though cognitively you know it doesn’t make sense, you would never tell anybody you love these things, your brain is interested in what keeps her safe.

Ashley: Right.

Lindsey: And if she rejects herself before she gives herself the opportunity to be rejected by anyone else, then we’re safe.

Ashley: Yes.

Lindsey: And so I think that the best place to start here is like, well, yes, if your nieces brought this to you, you’d be like, “What, you’re crazy. You’re out of your mind. Why would you do that?” But I think the first thing is being like, I’m so sorry you think that. I love you. Of course you think that you’ve been fed your entire life perfection and magazine models. Like you’ve been fed this narrative that your wrinkles, that your being passed 40 is not okay. Of course you feel this way, it’s okay. Like giving space for that.

What would change if you really offered yourself compassion for all these very human thoughts and your brain’s desire to keep you safe from this rejection?

Ashley: I mean, I would go out into the world just feeling accepted for just exactly who I am. I would probably be a little more confident, maybe shoot my shot, right? Knowing that that could be a possibility, not expecting it, but knowing that it could be and that that’s okay. And then you move on and you try it again if you want. Or there was a cute new guy at work, this is what kind of sparked this.

There was a cute new guy at work and I know that he’s just coming in, he has to be younger. I don’t know that for sure. We kind of smiled and looked at each other and I was just like, what are you doing? Don’t even go there, he’s probably way younger than you. Don’t even go there. And it’s like, whoa.

I’m not saying that this is somebody for me, but it’s like I am already writing him off because he’s too young. That’s the only way. Super cute, super nice, all these things, but it’s like I wouldn’t even go there because he’s much younger. And so anyway, that’s just kind of – I was like, wow, there’s something here that you kind of have to, yeah.

Lindsey: Well, let’s celebrate the awareness of that, right? Because most people would do that and not even notice it and just look at this like it’s a fact. Rather than you were like, huh, this is a block. I see that there’s another path.

So, again, something that our brains really want to do when it offers up these thoughts that we know don’t serve is as we like to give ourselves a pep talk or whatever and kind of combat them. And that’s not a problem, but again, the best place to start is that self-compassion.

Ashley: Okay.

Lindsey: I’m so sorry you feel that way. You’ve been told your whole life that you’re supposed to look a certain way, of course you feel that way.

Ashley: Right.

Lindsey: What it does is it gives you this really soft place to land. And with that kind of compassion, I’m just curious, do you feel like even though your brain is going to offer you these thoughts, you can still move forward with them? Does it feel different when you think about it from that viewpoint?

Ashley: Yeah, for sure. For sure it does. I feel, yeah, it’s just a much better feeling.

Lindsey: Right? It’s not like it’s gone, but you’re like that’s okay and we can still move forward.

Ashley: Right, right. And I’ve been out of the dating scene for a while, so that’s also kind of new. And it’s different now and it’s a little uncomfortable. But I do know that I need to try to get past this little block because I could be completely missing out on opportunities that could be good for me regardless, not even like finding my person. And that’s what I said, it’s not even about this guy at work. It’s more like what it brought up for me.

I guess maybe just, not constantly because that sounds negative, but just continuing to tell myself it’s okay. It’s okay. I’m thinking that this practice makes it easier or you do get, you know, the more I tell myself these compassionate things, the better that is, right? I’m just assuming it’s like a practice.

Lindsey: Totally. And I think the biggest thing is when you offer yourself that self-compassion, it doesn’t mean you don’t move forward. Just like, again, if one of your kids did something really scary and it didn’t go well, you’d be like, “I’m so proud of you. Of course you feel uncomfortable. Of course you feel embarrassed.”

Ashley: Right.

Lindsey: It just offers this space for humanness, rather than trying to shove it down and be like, you’re fine, you’ve got this, right? And then that makes it even worse, right?

Ashley: Okay, that’s true, yeah.

Lindsey: Then you’re trying to ignore all of this –

Ashley: Because you’re like, “I’m not really fine, but okay. No, I am fine.”

Lindsey: Yes, pretend we’re fine. Yeah, instead of being like, of course, you’re not fine. That’s okay. This is uncomfortable. This is scary, of course you’re afraid of this.

Ashley: Okay, wow. And there’s other parts of my life that when you had said if I reject myself first, then no one else can, like that is very powerful because I find myself doing that in a lot of other areas. It’s like, “You can’t hurt me because I already know that about myself.” And yeah, so I don’t know, that can’t be healthy either.

Lindsey: Well, I think it’s the same thing here. First of all, that’s very human. It’s one of our brain’s little tricks to keep us safe and not put ourselves out there and not be vulnerable. But again, it’s just like seeing what your brain is doing and being like, of course, you want to keep me from putting myself out there. You don’t want to feel embarrassed or disappointed or hurt.

But the more you offer yourself that, here’s what I’ll – Just to give you a little bit more understanding of how it works. It’s almost like you’re giving yourself a mother figure, I guess. I don’t know if that’s the best way to explain it, but it’s like you’re giving yourself a hug every time you’re afraid, and like understanding. And what that does is even though the emotions are there and they’re very real, it makes you feel safe to have them.

Ashley: Yeah.

Lindsey: And then when you feel safe, you’re willing to still go out and do uncomfortable things because your brain still will want to avoid rejection. And that’s the other thing that I think is important here, is this discomfort will be there.

Ashley: Okay.

Lindsey: We’re not just going to remove this entirely. Like over, not necessarily time, but as you work at this eventually you’ll become a person where you can’t even imagine even having that thought.

Ashley: Right.

Lindsey: But the way you get there is to offer yourself that compassion and do the uncomfortable thing. Like if you’re on a dating app putting the age range a little bit wider and for younger people and going on dates. And every time you’re like, “Oh, I don’t know, they might not like me, they might think I’m too old,” whatever, right? It’s like, I’ve got you. It’s okay. Of course you think that. Of course you’re scared.

Ashley: I remember we would question – Okay, so I go on a date and they say I’m too old. What does that mean? What happens then? It’s like, okay, then I’m too old to that person. Like keep on questioning it, right? And in the end nothing happens. I’m not going to die because someone thinks that I’m too old for them. It’s like, I don’t know, I’m just having all these thoughts of even our past conversations where I would just, “Why? So what happens then? Okay, so what does that mean? What does that mean?”

Lindsey: Yeah.

Ashley: And when you get down to it, it’s like rejection and feeling alone and feeling like no one likes you. But in the end, you’re not going to die. And that’s not true, I have friends. I’m sure I will find a great guy one day. So it’s like all those worst-case scenarios are not actually true. Like they could be, but they’re not, you know?

Lindsey: Totally. Well, I think the other thing is what happens when you reject yourself first? How do you feel then?

Ashley: Well, it feels safe, I guess. I feel safe. But I also don’t feel good. I mean, that doesn’t feel good.

Lindsey: Yeah. So if you think about it, you’re trying to avoid someone else rejecting you, but you end up rejecting yourself. So you just feel rejected anyway.

Ashley: Period, like that is it.

Lindsey: Right?

Ashley: Yeah.

Lindsey: But the other beautiful path here is that learning to have self-compassion and giving it to yourself every time you feel this discomfort, you start to show yourself that even if you’re rejected, you’re never rejecting yourself. You are always having your own back.

Ashley: Okay.

Lindsey: Here’s what I want to offer on the other end of the spectrum here really quickly. So this is going to be funny. So I don’t know if you’ve ever heard of Matt Rife, he is a comedian.

Ashley: Oh my God, yes, I love him.

Lindsey: My husband knows it. He’s like, you like this dude. I’m like, yeah. I’m like, he is so cute, so funny. All of the things. Well anyway, it’s funny, I don’t know how well this will go because he now has a girlfriend who’s young and all these things. But I once heard that he was like MILFs and like older women. And I just thought it was such a fascinating thing because I thought, like this guy is probably all about it. He’s like, I love older women. I love their – How do I –

Ashley: Experience and their wisdom.

Lindsey: Yeah, I love their bodies, they’re more feminine and curvy and all of these things. If you think about it, it’s so fun to think about the fact that there are so many men out there in the world who will have that exact same story line, who will just love the wrinkles, who will love – Like I think about that with my husband. He has smile lines around his eyes and I love them. His gray hair peppered. I’m like, you looked like a 12-year-old before, I’m so glad that. Right?

So it’s so fun to think about the possibility and the idea that there are going to be younger men who are like, I will pass on a 25 year old any day for a 40 year old woman. And think about how you’ll see yourself when you look at it from that lens.

Ashley: Right. I mean, that’s empowering. And that makes me feel good. And that makes me have a little pep in my step. Be like okay, yeah, no, I do got it going on. I do have more life experience than these 25 year olds and I don’t play the games, whatever, right?

Lindsey: Right? Yes.

Ashley: Okay, yeah, that’s good. That’s good.

Lindsey: So there’s this whole other avenue and that’s what your dream guy is going to be all about.

Ashley: Yeah. And I may – We’ll do something on the call because you’ve just sparked another thing. But yeah, this is good. This is really good.

Lindsey: For those of you listening, we’re talking about the life membership calls. So we’ve got hot seat coaching there, so she’s about to wrap this up on that call. But I think that the biggest thing here is self-compassion, creating that safe place for yourself by putting yourself out there and even when you have all those very human thoughts and problems and whatever.

I love the first sentence, “Of course. Of course you feel this way.” And then I fill in the blank, right? I mean, I don’t know if you’ve watched it, but there is a whole video in the life membership on self-compassion. So I would recommend starting there.

Ashley: Okay.

Lindsey: And then you create this solid foundation and then you get to sell yourself on this fun story that whatever age he is, the guy that you end up with is going to think you are floating on air. He’s going to be all about all of it.

Ashley: Okay, I love that. That feels so much better.

Lindsey: I love it. Well, thank you for calling in, Ashley. I will talk to you soon. I’ll see you on the life membership call.

Ashley: Thank you so much, Lindsey. Okay, bye-bye.

Lindsey: Bye.

If you want to call in to The Life Coach Hotline, go to https://lindseymango coaching.com/lifecoachhotline. Talk to you soon. Bye.

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