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!

Free Guide

Copy & Paste These
"9 Texts No Man Can Resist"

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

  • Love the quick-fire format, Matt – I agree with another poster, making it a monthly feature would be great.

    Gotta slightly disagree with you on the age-gap advice, though. As a woman who was with a younger guy for 12 years, it’s erroneous to assume that ‘because he’s younger, is he still going to want to be with me in 10 years’ time?’

    The error is assuming that *anyone* you’re with now will still want to be with you in 10 years’ time. Starting off at the same age is not a guarantee that either one of you won’t change or evolve, or won’t have a mid-life/health crisis which fundamentally shifts your world view, values or priorities.

    As the first responder here notes, guys appear to want younger and younger partners as they get past 40. Kids, responsibilities and just sheer *life* can have a detrimental affect on relationship longevity, wherever you’re starting from.

    To the 42-year-old lady who’s hesitating about dating the 33-year-old-guy; do you share the same values and background? Are his friends settled/settling down so he’s not bucking his social group’s trends? Is he generally attracted to older women? Do his actions match his words? Does he want kids soon/ever?

    Have some low-key dates, refrain from sleeping with him, gather enough data to make an informed decision. If he’s not able to make you happy, move on. But it’s often better to check out the reality of something than to run scared of an assumption and regret what ‘could have been’.

  • Hey matt. I cant thank you enought. I usually get emotional involved to fast. That answer was what i need it.

    Love this pull of q&a.


  • Brilliant! Thanks so much! Loved it!

    Mathew, is it true that if a man is interested in you you he’ll make a move after the first 3 times of seeing? Or is this a myth? Don’t some men need more time than others?


  • I’m 25 and a 20 year old has been trying to date me. I’ve been hesitant to give it a chance because he is so much younger. Ironically, I’ve also been asked out by a 49 year old guy. He has so much energy and is very confident about himself. Unfortunately, I have yet to go out with him. We’ve exchanged phone calls and such, but our timing has been awful. Since we werent able to get together on a date, he’s now dating someone else. I just wonder if he became hesitant the way I did with the 20 year old.

  • I love this format too. I’d been missing some Matt-input to the questions here. And Jameson (Hi Jameson!). :-)

    Before Get The Guy I had a good life but didn’t meet many men. I’ve decided I’m more relaxed and myself meeting people doing activities I like, rather than on the street (grocery store, Starbucks, etc.). My passions are cooking, yoga, volunteering with children, sewing, things that are very female-centered. I’ve tried doing a mix of things. Things I like and things men like to do, but I get bored at things that don’t interest me and I honestly only have so much time. I do try to be interested and have tried loads of new things in the past year, but I miss doing things I already enjoy all on their own. For example, I met a guy who was a Buddhist and went to a lot of Buddhism things with him which was his passion. After a few months, I had to tell him it wasn’t going to be my passion (I really tried) and we fell out of touch.

    So what to do? Continue with singles events/bars/things that don’t truly interest me but lots of men come to or focus on making myself happy with the female-centered activities I really love to do?

  • Hey Matt! Hi from Brazil again!
    Thanks so much for effort and dedication on the videos you put out. Every piece of information you give is really helpful and valueable.
    Cant wait for the next one!
    Have a great Sunday!

  • Hi Matt!

    This video was so timely for me, it was amazing! Thank you for your thoughts on how to trust again after an abusive situation – I watched the video more than once just to absorb what you said. Thoughts and behavior can be shaped – consciously or subconsciously – by an experience of abuse, even if it was in the distant past. Although being able to trust a man again can be difficult, on the other side of the coin is learning to trust yourself. Over the years I’ve learned instead of overlooking certain behaviors, to pay attention to my intuition and those “red flags” — they’ve saved me from a lot of additional pain and suffering.

    Thanks again – be blessed!

  • Cougar stereotype is uncomfortable.

    Agree with your video that age difference is significant. As a newly separated women, on the path to divorce, I find myself surprised and amazed that younger men are so aggressive. It is indeed a different world.

    I think value systems and family systems need to be congruent and age may be a best fit+/- 5 years. No man really understands why you have to suddenly leave him to fly across the world to check on your adult children, unless they themselves have children.

    But ladies, we do deserve to have some fun; so there is nothing wrong with a dinner or two as long as it is kept entertaining and light; they are often incredible amusing and romantic.

    1. Agreed. Fun is good.

      Where I think it’s dangerous is in overestimating what something is going to be. Something being a good time now is a poor measure of whether it will still exist 5 years from now. We have to be looking at a lot of other factors at the same time. x

      1. Matthew, you know I love you and am a massive fan since I first met you at your UK book signing. I was the one who mentioned Toyboywarehouse and age gap relationships, much to the amusement of others in the room- including yourself! :)As a woman who usually dates men 20 -25 years my junior (and has had a 2 year relationship with one of them), I have to agree with the comments you have made here EXCEPT that I think you should take out the reference to age gap relationships in them. Those comments apply to ANY relationship don’t they? Since I went to the women’s weekend I have given much thought to the importance of values and at last have identified mine and prioritised them. At the end of a 2 year relationship with a younger man, I realise even more the relevance of what you have said about values, and the importance of partners giving similar priority to similar values. I think this is the case whether there is an age gap or not. Truth is, I’m not fussed whether they are young or old- I am only interested in whether there is an attraction or not, whether our values are congruent, and whether we can have a good old laugh together. That seems like a pretty good recipe for a long and happy relationship to me. And just in case anyone is curious, my values are family, honesty, respect and compassion. I split with my lovely younger man because his were monarchy, country, britishness. I think this is a good example of why age is just a number and tells you absolutely nothing and for this reason is just not important to me. Muchos love x x

  • Yes thank you for this video. This type if Q&A session is very helpful. I would love it if you do more of these videos!:)
    One question I’m dying to get answered is:

    What guys perceive as a challenge in the beginning stages of a relationship?

    Thank you.

  • Thank you, Matthew, as always for your pearls of wisdom! We love what you consistently bring to the table for us !!

    But most importantly, thank you for helping me officially take you off of my “what if list” (you being the younger man) ;-)

  • Thanks Matthew! I really enjoyed this question and answer format and would love to see more of it in the future. Keep up the great work!

  • Hi Matt I have a question!

    See Im not the type of person that wastes ones time and usually in the first stages of the relationship I will go out for three or four dates and if I don’t see it going anywhere I call it quits. The relationship never just slowly dies, I usually cut the cord and end contact. Is there a more prescribed way of ending a relationship that you don’t see going anywhere and how long should you give the other person before calling it off??

    Would love if you would answer this question. I have been so misguided in this area, I’m sure other women are as well.

    ps Matt. I’ve been following you for sometime now and you have really built up my confidence. Thanks again.

  • Hey Matt, yes the age gap worries me.. What i notice when i am with men of same age category , there are similar reference points , yet we are not on same wavelength , unlike men younger than me . We may be in different points in life , but yet we can relate to many things together , the physical and intellectual chemistry( brainal) is awesome , which i find difficult to connect with men my age group .
    I have been badly burnt and bruised in my relationships . I dont have trouble ‘getting a guy’ but rather ‘ keeping the guy’ due to insecurities and the hand of life dealt with – a kid and age factor .
    I have lost hopes for myself and find myself settling For ‘Friends with benefits’ casuals . i crave for a loving caring relationship, i have learnt to numb myself of any feelings and emotions

    1. Hey Nina,

      It’s ok to want a loving relationship, but needing one to be happy is a different story. The first leads to proactivity, the second leads to desperation which scares men away.

      Remember, you don’t need a relationship to give you everything up front, you need to enjoy every stage of it. In other words, fall in love with the process. If you are open to the idea of it going somewhere if he proves himself, that’s healthy. If you are tied to the idea of it going somewhere, that’s dangerous.

      As for the friends with benefits thing, don’t give more of your intimacy than you are comfortable with. The key question is this: “Would I still be comfortable giving this part of me if it never went anywhere?”

      Remember to relax and enjoy every minute x

  • Loved this method of rapid fire Q&A. Would love it if you gave a heads up in advance so that people could send in their questions knowing you’d be doing a video like this. Thanks for all your lovely videos Matt!

  • Hi Matt,
    Loved your book! I was dating a man for ten years and waited patiently for him to pop the question. After hearing way too many empty promises and outlandish excuses (including that rising gas prices prevented him from saving for a ring), I finally bit the bullet and walked away. Fast forward four months later and I’m developing feelings for his best friend! We have so much in common and he is a man of his word who wants a family one day like me! Could this ever work? We don’t want to destroy their friendship but I also feel like I’ve sacrificed my happiness for way too long.

  • Hi Matt – you’re the best! You’re advice is spot on. Question – can you provide a serious discussion on why men might not be able to perform in the bedroom once you both decide its the right time? My last three relationships with younger men (28-36 yrs old, I’m 38 yrs old), they have had performance issues and they have all said I make them nervous. They are saying this in a “complementary” way, but at this point its not feeling that way. My other experiences in my younger years….never had problems with partners, actually the opposite affect…had partners always “turned on easily” by me. Thoughts?

  • It is a brilliant idea regarding a quick-fire video. However, I would like you Mathew to elaborate on friend zone concept (whether it is worth to try to get out of it and if so how to do that).

1 2 3 4

Leave a Reply

Your email address will not be published. Required fields are marked *

All-Time POPULAR Posts