Expert Advice Before Your First Time Dating Younger Men

Welcome to the #365Firsts Podcast and the Expert Advice Before Your First Time Series. The show aims to encourage, prepare, and inspire you to do things you’ve never done before and complete your #365FirstsChallenge list. 

In each episode of this series, we give you tips and advice to set you up for success, for specific firsts and new experiences. The guests and topics are as varied as the options and possibilities of new experiences. 

Whether you’re trying to learn a new skill, improve your health and happiness, work on your self-development, add excitement and adventure to your life, or simply have first times, you’re going to love our podcast.

In This Episode

The world of dating is constantly changing, evolving, and filled with opportunities to do things differently or for the first time. Many of those changes, aren’t immediately accepted, take online dating for an example. When it first started, many people thought it was crazy to meet strangers online and then go out with them in person. Now, online dating is a normal thing and the most popular way of dating.

Another shift in the world of dating that has become more common lately is older women dating younger men. Older women have faced a lot of discrimination and stereotypes within the dating world historically, yet a lot of them are reclaiming their power, and opting for dating situations that make them truly happy. 

In this episode, we were joined by a guest expert who knows a lot about dating and romance in general. Together, we discussed everything a person needs to know about dating a younger man for the very first time.

The Guest Expert

In this episode, we were joined by Susan Winter. 

Susan is a best selling author of Older Women, Younger Men: New Options for Love and Romance and has been featured on Oprah. She is a relationship expert, and specializes in evolutionary forms of loving partnership and higher thinking. Susan writes, speaks and coaches on accessing out inherent perfection in life and love.

Susan has been featured on the Today Show, Good Morning America, ABC/CBS/NBC evening news, CNN and BBC. In terms of print, she has been featured in Harper’s Bazaar, Cosmo, People Magazine, Forbes, the London Times and the New York times. When it comes to radio, Susan is a frequent guest on NPR, BBC, ABC, PLAYBOY RADIO (Sirius) and CBS News.

Her podcast, The Susan Winter Show can be heard on iHeartRadio. Susan also has a very useful YouTube channel, packed full of rich content and useful advice. She’s got so much information and expertise to share in the world of relationships.

What You Need To Know About Dating A Younger Man For The First Time

Susan started off the episode by describing her experiences with dating younger men, and noted how stereotypes surrounding older women in the dating world can be very harmful. There is less of a stigma surrounding older women dating younger men now, thankfully, but it does still exist and can be distressing to deal in person.

Be Willing to be Open-Minded

To start off with, Susan encouraged women to be open to the idea that they can date younger. Don’t let preconceptions and negative stigmas stop you from finding somebody that makes you happy and feel good. You are entitled to happiness with a younger partner, no matter what traditionalist views or onlookers might say.

Addressing Self-Doubt

Susan acknowledged self doubt and body image issues can be prevalent if you’re with a younger partner. She noted it takes a significant amount of confidence and self love to be able to wake up to a partner that’s 20 years younger than you.

One of the main things that can stop a woman from pursuing a younger man is the fear the situation might change too quickly, or that a younger partner might lose interest in them. This can be hard to deal with, and Susan encouraged women to have greater confidence in themselves when facing these negative thought patterns and realize/believe their partner are attracted to them for a variety of reasons.

Be Ready to be Valued

Something that’s great about dating younger men is that they are often a lot more supportive and proud of a woman’s achievements. The power and drive of an older woman can actually be incredibly attractive to a younger man, as can incredible conversation and content too. Younger men who are into older women are often much more confident in themselves as a person.

Addressing the Question of Children

Children are one of the main things that can affect a relationship with an age gap, and it’s worth making sure you know what type of partner it is you’re dealing with before starting a relationship. Does your partner want children, and do you? This is something extra important to discuss with a partner before initiating a long term relationship, when an large age gap exists, because there are limits to being able to align the possibility of children together.

Susan identified there are three types of men when it comes to having children. Some men will value a woman above all else, and consider children as an afterthought if it makes their partner happy. Some will value children above a partner, and others will be indifferent to the idea as a whole.

Understand the Partnership Dynamics

Power should be considered in a relationship, and it’s important to acknowledge that a younger partner might have more power and experience than you give them credit for. Just because you’re someone with a house, savings and life experience doesn’t instantly mean that you’re going to be the dominant one in the relationship.

Of course, there are always going to be differences when it comes to dating younger men. 

There are going to be differences in opinions and pop culture experiences, for example, and with hobbies and pastimes too. It’s worth embracing these, as they can make a relationship so much more interesting to be in.

When it comes to the physical aspect of your relationship, it’s important to remember that younger men will be interested in you as an entire person. Try to be as present as possible, and be willing to try new things with your partner as well. Some younger men may be more experienced than you, and others may need more guidance.

Overall, the most important thing that Susan encouraged is the importance of being open-minded. No matter if you’re currently dating a younger person or are simply considering it, just try to embrace new experiences with an open heart. 

It may work out for you, or it may not be the right thing for you- but trying can be very rewarding.

Get In Touch With Susan

This episode was certainly illuminating, and we’re grateful we got the opportunity to speak with Susan about her work. If you’d like to find out more about Susan’s work, her website is and her social media links are as follows;

If you want to ask Susan any questions about her work or anything she said on this episode, we’re sure she’d be more than happy to speak with you. 

How To Reach Us  

If you’d like to give us feedback on our show or let us know what you thought of this episode, we’d be thrilled to hear from you. No matter if you have something positive or negative to say, it’s always important to us to hear back about our work. 

Is there something, in particular, you want advice on? Are there things you think we could be doing better as a team? Please feel free to get in touch with a member of our team at today.

What’s Coming Up Next Time?

New episodes of Expert Advice Before Your First Time are released every Thursday, and we’ve got a wonderful roster of guests lined up to give you more expert advice. 

On the 14th, we’re going to be speaking to Lauren Gibbs about bobsledding for the first time. After that on the 21st, we’ll be learning about volunteering for the peace corps for the first time from Jen McFarland.

You can listen and subscribe on Apple, Google, or Spotify. While you’re there – please leave a review if you can. It really does help us with our work, and every single review is appreciated.

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