12 Tips For Younger Men Dating Older Women

Updated April 8, 2024by Regain Editorial Team

Being in a relationship with an older woman—who might be self-assured, experienced, and established—can be both fun and fulfilling. While dating an older woman as a younger man can be exciting, the age gap can also present specific concerns. Knowing how to navigate potential pitfalls can ensure your May-September relationship is thriving and mutually beneficial. In this article, we’re discussing tips for developing a rewarding age-gap relationship as a younger man. 

Tips for younger men dating older women

According to one survey, 34% of women over 40 are open to dating younger men. This means that if you’re also open to an age-gap relationship, you may find yourself with plenty of opportunities to date an older woman. For those who are interested in such a partnership, the following tips can help you ensure you are both engaging in the relationship in an open and healthy manner.  

1. Set clear expectations

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Though not always the case, an age gap might mean that the older partner has more experience dating. An older woman might've had several relationships and even been married. This means that she likely knows what she wants out of a partnership. So, it can help both of you to set out some expectations as you start dating. 

Be upfront and honest. Discuss what you're looking for, how you'd ideally like the partnership to progress, and so on. Make sure that you're as honest with yourself as you are with them. If you want a fling and they don't (or vice versa), the best way to show respect for your partner is to acknowledge your preferences and have a candid conversation with her. She will likely appreciate your forthright attitude. 

2. Be open with your emotions

Showing affection, regardless of your or your partner's age, is healthy. You may feel that, because your partner is self-assured and independent, she’s less interested in imparting emotions or having you do the same. But showing your emotions and being vulnerable with your partner can help you bond on a deeper level. She will likely see it as a sign of maturity that you’re able to discuss your feelings.  

3. Be mindful of her time

An older woman might have a busy schedule that makes alone time with you difficult. She may have kids, a career, or other demanding obligations. So, while you might want to go on spur-of-the-moment dates or text her often, try to be considerate of her time. For her, quality may come over quantity. As a younger person, you may be used to making plans on a whim; but with an older woman, consider setting dates well in advance so that you’re being respectful of your partner’s time.

4. Constructive communication is key

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Effective communication, as we’ve discussed already, can be particularly important in an age-gap relationship. You will want to be able to communicate calmly and take accountability when needed. If issues arise that need to be addressed, try to bring them up with your partner right away. For example, if you find that you’re uncomfortable spending a lot of time with an ex-spouse—a situation that may arise when dating an older woman—it is usually best to tell her that as soon as possible. This allows you to stay on the same page as the relationship progresses and keeps you from having your feelings hurt. 

5. Be yourself around her

This is one of the easiest things that you can do, but it's necessary. Avoid letting the age gap keep you from being who you are. Sometimes, if there's insecurity surrounding the age gap, it can be tempting to try to overcompensate or be something you aren't. In an effort to stay on her level, you may try to behave in a more serious or refined manner, which can be great—to an extent. Remember that you're attracted to each other for a reason. She may appreciate your youthful enthusiasm and easygoing attitude. 

6. Be prepared to interact with kids

If you're dating someone older than you, there's a higher chance that they'll have kids from a previous partnership. One thing you may be concerned about in a May-September relationship is that you might not have much experience with kids or dating someone with kids. In addition to giving her the time and space she needs to be with her children, you may want to check in with your partner and ask how much time and involvement she wants you to have with them. At the beginning of the partnership, there might be quite a few boundaries about how involved you are in the lives of her children. 

If she’d like you to meet her kids, you might want to prepare yourself for interactions with them. It can be important for you to not confuse her children by trying to take the place of a parent. You may want to avoid trying to get close to them too quickly. Since you’re a new person in their lives, it may take a while for them to connect with you. Your partner will be the best reference for how to interact with her kids in a healthy way. 

Another potential family-related concern, of course, is that they might want to have kids or have additional children sooner than you do. Be upfront about this, especially if it isn’t aligned with what you want. This is relevant regardless of age, but when you and your date or partner have an age difference, it could feel more pressing. 

7. Be self-aware

When you enter a relationship, your actions impact another person, emotionally or otherwise. When you start dating an older woman, it can help to look at your patterns in past relationships. Is there anything that you can improve? Something you wouldn't want to repeat? Try to be self-aware and use your knowledge as a guide for the areas in which you can learn and grow. Being able to admit your faults is a sign of maturity, no matter how old someone is. 

8. Have your life together 

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If your partner is established in certain aspects of their life—maybe they have a career, financial stability, etc.—she may want you to bring similar qualities to the table. Of course, this doesn't always have to do with age, and certain things don't necessarily have to make you incompatible. For example, it might not be a dealbreaker if you're mature and love kids but aren't employed at the moment. Try to look at your current situation objectively. Are there areas that you could improve in order to provide stability to a relationship with an older woman? This could help her feel more stable and close to you as you move forward with your partnership. 

Navigating an age-gap relationship with therapy

Studies show that online therapy can be an effective form of counseling for couples who are facing situations that may lead to relationship distress, such as an age-gap relationship. For example, in a study of 151 couples, researchers found that online therapy led to improvements in relationship satisfaction, quality, and confidence—gains which were sustained at both a 3-month and 12-month follow-up. Participants in the study ranged from 21-65 years old, suggesting online therapy may be beneficial for partners of widely varying ages. 

Online therapy is available if you and an older partner would like to talk through challenges related to a May-September relationship. With an online therapy platform like Regain, it's easy to get paired with a knowledgeable and compassionate licensed professional. Regain works with thousands of licensed therapists—who have a range of specialties—so you’ll have a good chance of working with someone who can address your specific concerns about an age-gap relationship. Your therapist can also connect you with useful resources, such as at-home exercises that can help you better communicate and develop a strong bond. 

Therapist reviews

"My girlfriend and I have been working with Alison for about four months now, and with her help and guidance, we have strengthened our relationship tenfold. Her communication style is amazing, and she strives to make the best of our time with one another. If you're looking for a counselor you can put your faith in with the whole experience, she's the one to go to."

"With Cassandra's help, we've been able to bring our relationship to a new, healthier, and much happier level, working through painful situations, growing as individuals and as a couple, and with tools to stay on this path. She's very responsive, and it has been great to have her facilitate our messaging through the app all week. I highly recommend Cassandra. She's skilled, supportive, and down-to-earth. We feel comfortable with her."


Being in an age-gap relationship as a younger man can be a rewarding, meaningful experience. By keeping the above tips in mind, you can connect on a deep level with an older woman. If you have questions about being in a May-September romance or experiencing similar relationship concerns, consider reaching out to a professional through online therapy. With the right support, you and your partner can continue to build a strong relationship at any age. 

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