Dating Tips

Should I Start Dating a Much Older Woman?

To anyone who is new to the dating scene or has spent the majority of their time dating within their own age group, it can seem like a strange step to start dating an older woman. However, there is nothing strange or weird about it, and not just because plenty of guys have dated older women than themselves. There are plenty of men who like cougars because of the wonderful partners they are and the beauty of these ladies. If you believe you may have a thing for older women, then there is nothing to be ashamed of. Admiring a woman’s beauty is natural, and pursuing a relationship with these ladies can be very fulfilling romantically. For anyone new to this area of dating, you’re in luck as we have help and advice to help you navigate through this environment.

couple hugging woman is happy

Do Guys Like Older Women?

The very short and simple answer is…YES! There is no harm in dating, being attracted to, and falling in love with an older woman. As the old saying goes, the heart wants what the heart wants. Many men want to explore these kinds of relationships but can be held back, one of them being that they believe there is a stigma attached to it. However, plenty of guys seek out older women for relationships without fear, and some of the reasons to date an older woman include:

Attraction & Beauty

Women aren’t just beautiful in their younger years! Beauty isn’t attached to the world’s standards of what it is, and many older women retain a natural grace to their look. Naturally, this inherent and elegant beauty attracts many younger men to them, especially as they may look very different from women of the man’s age group. They are more likely to have their own sense of style and find things that suit them, which makes a woman very attractive.

Plus, many guys are just simply attracted to older women. Attraction is an odd thing in that it can’t be quantified. You may think you like blondes, Asians, or girls with a certain body type, but attraction doesn’t fit into those qualities but rather what the world tries to tell you is attractive will. It is up to you to follow your own desires and pursue what you want in life.


Most older women tend to be more self-assured and confident than their younger counterparts. Over the years, they have learned how to be more assured in who they are and take what others say with a pinch of salt. This confidence is incredibly sexy and appealing to younger men, especially those who may have been in relationships with insecure and anxious girls. Many guys like the thought of being with a woman who will feel secure in their relationship, meaning they can focus on having fun together and getting to know one another more.

Emotional Maturity

Older women are likely to have been in drama-filled relationships and have learned a thing or two over their time. This means that they are more likely to discuss situations and communicate effectively instead of flying off the handle about a situation. They often know how to approach a difficult subject and how to talk about their feelings without letting it consume them, which helps create a much more balanced and secure relationship.


This experience is impactful in every area of life, from conversation to finances. A lot of younger men appreciate that their partner can handle themselves and is acquainted with the best ways to overcome challenges in life, in their relationship, and with others. This experience can also help a lot in the bedroom as lots of younger men enjoy a sexually experienced woman.

Am I Falling in Love with an Older Woman?

couple embracing outdoors near building smiling

Likely, if you’re here, there is somebody you’re thinking about romantically and, possibly, believe you’re already forming a strong emotional attachment to them. To help you understand your potential feelings, we highlight some of the common symptoms that suggest you’re falling in love with an older woman.

Do You Get Excited at the Possibility of Seeing Her?

Has someone invited you to an event, and your first thought is of seeing her? Do you make sure you go to certain weekly activities just to spend more time with her? If this is the case, then it is likely that you’re falling for this woman. Naturally, as you want to pursue a relationship with her, you’ll want to be in her presence; this is only natural. However, don’t get too carried away with this but don’t act like a jerk. She is a human being, and you should give her the space she needs while also showing a genuine interest in who she is as a person.

Are You Looking for Reasons to Message Her?

Instead of just seeing something and thinking of her, you may be actively looking for something to message her about. Perhaps you know that she loves antiques, so you make a conscious effort to go past a store to send her a photo. Or you’re searching for puns because you know they make her laugh. Just as with the previous assumption, if you’re starting to have feelings for her, then you will want to keep in contact with her as much as possible.

When You Think About the Future, Do You Imagine Her in It?

This will be a massive indication of whether you are beginning to form a deeper connection with an older woman. Naturally, you won’t imagine huge life events being spent with just anybody. These are often reserved for people we have an emotional and mental connection with as well as just physical, therefore indicating that you’re developing genuine and deep-rooted feelings for her.

How Often Does She Enter Your Mind in a Day?

As you begin to become more connected with someone, they will enter your mind more frequently throughout the day. Not just at night when, perhaps, you’re a little bit lonely but as you see a pretty flower on your walk. It doesn’t take us long to think about the things we love and cherish, so if you’re thinking about her a lot during your day, then you could be falling in love with this older woman.

Are You Attracted to Her?

Love isn’t based on attraction – it needs to be deeper than that – but before we fall in love, we have to be attracted (in some form) to that person to make us want to build a deeper connection.

Why Do Men Like MILFs?

smiling pretty mature woman using mirror

Another category within the older women department is MILFs, a separate entity from purely liking an older woman. A mature woman lover will be attracted to any older woman, but someone interested in MILFs specifically wants someone who is a mother. Furthermore, there is a much more overtly sexual element to this attraction as it plays into the sexual fantasy aspect of being with an older, potentially married woman, and it can be an everyday scenario but turned into something more. Some of the reasons men like MILFs include:

Sexual Fantasy

Porn and overtly suggestive material are extremely prolific these days, and they can very much inform what we believe we should be attracted to or what will seem to satisfy us. The idea of being with a mother can fill a pornographic fantasy as it turns an everyday situation into something sexual. While not every man will pursue a woman with kids, for this reason, it is wise to ask yourself whether you’re simply looking to satisfy lust or whether you’re genuinely interested in these women.

Caring and Kind Nature

Men who simply veer towards dating these kinds of women may be driven to these women because of their caring and nurturing nature. A lot of men have to face adverse circumstances and be strong every day, which is why it is nice to have a woman by your side who will comfort you and act kindly even when it seems as though the whole world is against you.

Responsible and Mature

Mothers have to take responsibility. They cannot function in their role if they can’t act maturely and responsibly as there is another life depending on them. This often translates to other areas of their life and can be incredibly attractive to a young man. He knows that the woman he is with can handle herself and take responsibility for her actions while acting maturely about those decisions. There is less likely to be any drama, and the relationship will be able to maturely work through difficulties and challenges.

She Knows Herself

Dating someone who is strong in themselves and knows who they are is incredibly attractive. You can have fantastic conversations and dive in deeper with one another. After all, it is not all about appearance, and that will only take you so far. She is likely to be more confident about her personality, appearance, body, and the amazing things she has to offer. She knows her worth, and that is incredibly attractive in a woman.

Dating an older woman is a dream of many young men for many reasons, but always remember that this is your own choice, no matter what other people say. Just accept your feelings and make your woman happy; who cares about something minor as age difference?

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