Is It A Bad Idea To Date A Younger Man?

Is it okay to date younger men? How can you trust guys (in general) after an abusive situation? How do you not get emotionally attached too early? What to do with exes?

I’ve picked a mixed bag of questions from the blog and Youtube to answer in today’s video.


So we thought we’d do something a little bit different today, me and Jameson, rather than coming to you with a preconceived idea of what we wanted to talk about. We thought we’d listen to you and the things you want me to talk about and we’ve pick some questions both from the blog and from YouTube that we want to answer today.

It’s going to be quick fire, obviously we’re going to try and get this done in a couple of minutes so I’m not going to spend five minutes on each question. But let’s see what we can do.

“Matt, can you do a video on age difference in relationships? I am 42 and a guy that is 33 asked me out, I’m hesitant because of the age difference, thank you.”

Here’s the problem with the different age group: They don’t have the same references necessarily as you and they’re not necessarily in the same part of their life. Not necessarily because sometimes they are in the same part of their life.

Very often when a guy who’s in his late 30s decides that he wants to meet a 28-year-old woman, they might be in same place of wanting to settle down. But it doesn’t necessarily means they are on same wavelength and that’s when the danger comes in.

So when you start to date someone like that, before you even get involved, you have to ask yourself: do I think that this person is really someone I could be with? And am I willing to take the risk that 10 years from now they won’t be in the same place as me?

Now, one school of thought is, love is love and you can’t help who you fall in love with and you have to just go with it. That’s certainly true in some cases and there is some romanticism to that, but we also have to apply pragmatism to every situation and say, is this an unnecessary risk I’m taking at this stage?

Do I like this person enough? Do I really think that it has so much potential that I don’t mind the age difference? You have to be smart as well cause let me tell you something: the guy won’t be smart for you.

‘The age difference is too much, I really like you, but lets us keep out the distance because of the age difference.’

He won’t do that, especially the younger person of the two won’t to do that. He’s more likely to be reckless or she’s more likely to be reckless if she’s younger or if he’s younger. So go in eyes wide open, if it’s really important and you think it can work, go for it, but be aware of the risk involved.

“Matthew, what have you got to say for men who abuse women and how a woman can trust another guy again?”

The most I can do, unfortunately, is apologise on behalf of all of the men that actually have backbones and don’t abuse women, who tend to get a bad name from the guys who do.

I don’t think we should waste a second of thought or energy on men who abuse women, but what I do think we should do is answer the second part of your question which is about how to trust again; how to move on as a woman. That’s a great question.

The truth is, you can’t go on saying, ‘well the next guy won’t be like that so that’s why I am going to change’ because it’s that very thought that stops women from changing in the first place.

You will never convince yourself that the next guy won’t be like that because truthfully you never know.

They might not be abusive in the same way, they might be in a different way.

The point isn’t the next person won’t be like that, the point is what type of person do you want to be in this life? Do you want to be someone who lives out the rest of your life afraid because of what one guy did to you, or what two guys did to you or whatever?

In my opinion, if you’ve been abused before you shouldn’t be lending any more power to those people and one unfortunate way that people lend power to the people that abuse them is by continuing to allow it to affect them afterwards; to continue to avoid relationships, to make themselves unhappy, to feel self loathing or guilty in some way.

Instead take your power back by actually going to the next relationship with a clean slate and saying ‘you know what, I know that I’ve got some fear, I know that there is the potential for someone to treat me badly, but what I do know is that: A, I would never put up with it in the same way as I put up with it last time and B, I don’t want to be the type of person that avoids situations just because I am scared and just cause of some prick who in the past didn’t treat me right. I’m going to go and get my happiness regardless.

This next question is from Cookiebear99…

“I’m not sure if you would read this but I’ve got an important question. How does a girl not get emotionally attached too early?”

It’s hard, especially when you combine feeling lonely with the desire to be in love. It creates this potent cocktail which leads to you now overestimating the person you’re with, projecting an image you want them to have onto them instead of waiting for them to show you, and really expecting too much from them in the early stages.

Don’t be pessimistic in the early stages, but don’t be overly optimistic either. In other words, see them as they are. When a guy invests in you, value the investment he has given you not the investment you think he could give you. When he shows you what a kind person he is, or he shows you a fatherly quality that makes you think he could be good with kids, see it for what it is in that moment, not for something it could be in the future.

That way you are going to value what he has invested, you’re not going to value what you think his potential could be.

This last question is from Sophie…

“I would like to request that you make a video on how to get back with an ex smoothly, without looking desperate and clingy.”

Kind of a desperate and clingy question…

Get your ex back advice I find kind of icky, kind of.

Really the only reason you should be going back after your ex is if you feel you really messed up and you are supposed to be together and you need to show them that that part of you has changed cause really that’s the only thing they need to know to want you back again. In which case go find a way to spend time with your ex, whether it’s in a group setting, whether it’s calling them up and saying, ‘hey look lets just go and have a coffee’ or ‘I just want to hang out and see you, I miss you’.

You’ve got to find a way to not put the pressure on but to actually spend time with that person again and when you’re with that person spending time with them, you’ve got to be able to convey that that quality that wasn’t working for them before is different in you now.

But, I’ll add this caveat, don’t change your value system for that person if it didn’t work before, don’t change something that’s fundamental to you at your core, only do it if you know it was a bad habit on your behalf and you need to change it because it would benefit your life anyway to change it and it just so happens that it would also make you more attractive to your ex, and maybe re-spark the relationship.

That’s it, otherwise move on. There are plenty of great people out there, you don’t need to be overly focused on your ex.

So that’s it. Four quick questions. Let us know if you enjoyed that, if you want us to do more questions like this where we just quick fire a few answers. We won’t do it every time obviously, but it would be fun to do this a little more often and really get involved in some of the questions that you guys ask each week.

Speak soon guys.


What one questions would you like to see me answer in a quick-fire video like this? Let me know in the comments below!

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93 Replies to “Is It A Bad Idea To Date A Younger Man?”

  • Hi Matt! Love this new bite-sized format–very easy to digest. Keep it coming!

    My request for the next video/question is actually one to help me help my friends. I’ve got lots of girlfriends who married or in serious relationships who have been out of the dating game for a while. Although they are super sweet to try to set me up with men, they just don’t quite understand the right way to do it. I personally dislike being introduced with “You two would be so perfect for each other!” And then my girlfriends just sit and stare at us to see if a connection is made…#awkward! This removes the male instinct to hunt the woman, like you’ve talked about so much. I’d rather do a million blind dates than have a guy forced on me again. How can I help my friends without being a jerk? What’s a good way for them to introduce two people and still let them feel like they are choosing each other?

    Any advice is appreciated. Thanks so much!!!

  • Thanks for answering our questions Matt. I’d be interested in extended verbiage on dating younger men. Or more precisely, why some women attract them. Because I pretty much agree with what you said, but, what if they’re your only options? How do you fix that?

    For example, I’m in my early 30’s, but look like I’m 23-25 (so everyone tells me). So far in life I only seem to attract guys that are between 22 and 25, or occasionally older than 40. Kind of like what you said, I don’t mind dating a few years older or younger if we’re on similar wavelengths, but that’s almost 10 years either direction.

    I’ve been called an “old soul”, a “goofball”, love to learn/read, rarely drink, never had a one-night stand, and while I love to dance, there’s no table top dancing or stripping antics, so I can’t imagine it’s because these guys think I’m a party girl. In fact I’ve been called “the marrying type” more than once. But ya can’t get married if you’re attracting the not-in-a-marriage-mode type, ya know? ;) I’m open to the idea that it may be something I’m doing but I have no idea what…

  • hey Matt, I’ve just recently discovered your blog and many of your philosophies confirm what I have been learning which is men dont make the moves!!!!!!! Although frustrating I have my eye on someone and am determined to be proactive but I would only have one opportunity at a party. what is an effective but subtle way to get someones attention amongst a crowd

  • I loved this video (I love all your videos), and I would love to see more like this. Here is my question: what do you do about a guy who says he doesn’t want a relationship with you or with anyone right now, but then he keeps reaching out by email and then calling?

  • I think this short video is great Matt, it answered some questions very concisely and that is what you need sometimes, some quick answers! Thanks

  • This was a great idea! and I have been dying to ask you some questions that relate to work relationships!

    So I am new to NYC and only know my roommates (who never seem to want to do anything). I started making friends at work, but it seems as if everyone is already in their routines when it comes to what they do on the weekends or outside of work? What or how do you suggest I go about making new friends outside of work when I normally go exploring or what not by myself?

    As far as actual work relationships go, there are a couple guys at work that I would love to get to know better. Not sure if it could turn into anything more than friendship, but I really want to find out. How do I go about asking or seeing if there is potential for anything? I have tried the “a few of us go out every other wednesday, next time you should come with us.” But week days never seem to work out, then by the time the weekend’s come they already have their normal routines.

    What can I do to stand out enough for even one of the guys to want to spend time with me instead of his normal group of friends?

    Please help! haha


  • Hey Matt,
    Great video!!! I love the Q&A!!!
    perhaps you could give your opinion on why some married people have the audacity to pursue relationships outside their marriages.
    I recently started dating some guy 6 weeks ago and things were going good we hung out, went to the movies, out to lunch and dinners, he even spent the night once at my place (nothing happened. Thank God!!!)
    Anyhow things started feeling odd on a gut level and then I found out he is married. I did confront him about it and he said that him and the misses are not doing so well in their marriage and that he didn’t think I’d mind…WTF!!!
    Do I look like I want some second hand BS? Do I look like I’m dragging my self-esteem behind me on the ground?
    FECK NO!!! I’m so pissed right now!!! and I feel just awful for his wife to be married to a scum like that…

  • Hey Matt,

    Thank you so much for this video, I loved the “answering questions” idea!! Some of the questions were ones I wanted answered. You’re so great at what you do, thanks a lot!!


  • I’ve never understood the whole getting back with your ex thing. I have girl friends who do it all the time mainly because they would rather be with the wrong guy then try to find the right guy. My brother seemed to have a bad habit of doing that too but finally stopped when I introduced him to his wife. :)

  • I always love your advice! I have one question that I hope you can feature in a future video/blog post:

    Thanks to your great advice from the videos and book, I am developing more confidence in myself and I am now in a relationship with a guy I really like. However, he has a best friend who is extremely negative and insecure; she has all of the qualities that I have been trying to avoid for myself. Ideally, he would want us all to become friends and hang out often. How do I approach this situation without exposing myself to her negativity?

  • Wonderful idea for the vids! Love it! The questions and answers about younger men and exes hit particularly close to home for me. If I could ask a question, it would be about how to get over someone you really loved but wasn’t good to you. I’m a year past the falling off of a messy but meaningful-to-me relationship, but I still have times of grieving, especially after accidentally bumping into his family members or friends out in public. When that happens, I feel like maybe I haven’t come nearly as far as I wish I were. I’m at a loss for what to do next aside from continuing to challenge myself in other areas of my life, but those are mainly distractions from this problem area, I think…

  • RE: ABUSE. Get a therapist and work out how/why it happened and where your involvement is there. Did your family background condition you to expect less? What happened to give you a ‘Bastard Radar’? Have you still got it? How did you miss it first, why did you accept it for however long it lasted? Do the men you ‘pick’ subconsiously match one of your parents? There’s lots to think about and a good therapist will help you do that. I know my ‘BR’ got me into situations but learning from it has put me in a place of my own power. Now an abuser can’t get past my boundaries, my line in the sand. If therapy costs, buy a good book. Go online and reasearch this type. Get yourself sorted, then good love will come if you want it. You are not the only one if you experienced this but you will learn, survive and be better for it.

  • Hi Matt! As always a good video. My question would be: You always talk about the men and women relationship in a long-time relationship or trying to get that. But what about fuckbuddies, one night sex and that kind of things? I´m interested in what you have to say about that and your tips.

  • Hi Matt,
    Loved the quick-fire video very informative. Hey matt I am the ultimate hopeless romantic. My problem is I am 50ish and look 40, so I am told I have lead a very clean life. So the men my age are all “OLD” with one foot in the grave. I don’t want to be someone’s nurse. I totally understand the age thing with being on the same page. What’s a girl to do?

  • Hi Matt. Love what you’re doing, appreciate if u can take time for this. I do agree n thank you for what u share.

    What do you think about asians that grow up in asian country?
    or even some people that speak different language, i find it harder to express n carry the confidence for the linguistic proficiency.

    And I’m speaking generally no offense at all, does westerners look down on asian?

    As the cultural ,mentality, the way they perceive things do have some differences, most of us i would say. I really looking forward to know what do you think abt this or even if i make sense.

  • Hi Matthew,

    I could really use your advice about contacting a guy after you meet.

    I was at a party over my Christmas break from grad school with my mom and her fiancé. It was at the house of my mom’s fiancé’s coworker. They all work in the military. There was an incredibly good looking guy there about my age. The host of the party comes up to my mother and I and tells us how this young cute guy is a “real stud” and how he is special forces and super elite and going to Afghanistan soon. A little while later the host waves me over to meet a man who turns out to be the father of the young guy. The first thing the father does is ask me if I have a boyfriend. Then after some more obvious interviewing he calls over to his son standing behind him and introduces us.

    He was very smart, funny, cool. He kept asking me questions. Telling me about his training to be a soldier. What other careers he is interested in. How much he loved school, etc. There was a table between us. He moved around the table to get closer. He made direct eye contact the whole time which felt overwhelming. Everything was going great, and then all of the sudden he looked real anxious and said “I have to go to the bathroom, be right back.”

    I stayed in the general area and started talking to other people. He came back, but we didn’t make eye contact, and he circled around a few times not talking to anyone. Then he went to talk to his mom and dad.

    5 minutes later, my mom and her bf say we are leaving. The cute guy’s dad instantly comes up to me and tells me how excellent he thinks I am and good luck. His son comes over and just looks me in the eye intensely again but says nothing while his dad is saying this. I say nothing cause I’m an idiot and a little overwhelmed with the dad.

    And that’s it. I found him on Facebook but did not friend him. He seems like one of the more impressive people I have ever met. I don’t know if I should do anything at all.

    Can you help me?

    Thanks so much,

  • Hi Matthew! Thanks to your awesome insights I have solved some of my issues about this great guy I have met. So thanks! :) This may sound like a dumb question but I’m still pretty young and new to the dating scene, but how do you know when you are in love? I ask for future reference of course! I just don’t want to say it and then realize I made a mistake!

  • The chemistry of mind is different from the chemistry of love. The mind is careful, suspicious, he advances little by little. He advices “Be careful, protect yourself” Whereas love says “Let yourself, go!” The mind is strong, never fells down, while love hurts itself, fells into ruins. But isn’t it in ruins that we mostly find the treasures? A broken heart hides so many treasures.
    ~ Shams Tabrizi

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