How to navigate dating effectively – for mature women + baby boomers

With divorce rates higher than ever before and Baby Boomers hitting their 50s, 60s and up, more and more mature women are finding themselves single and facing the choice whether to go back into the dating pool or not. Social mores and the media do not make it easy for older women. While older men are still often conveyed as sexy and desirable, older women are usually given a shelf life. While it seems to be common and socially acceptable for older men to date younger women, an older woman dating a younger guy is called a “cougar.” Why aren’t men given derogatory nicknames for doing the same thing a woman does? None of this helps, of course, when a mature woman is considering going back into the dating pool. That is why I think it is so important that women work on addressing their mindset before venturing forth into the dating world. Otherwise, it can be brutal!

I have two friends who started dating again in their 60s, and so I got to witness their whole process around dating on a very close and personal level. This is what I learned.

First, the timing has to be right.

One of these friends, whom I’ll call Andrea*, had spent many years grieving an old love and was finally ready to move forward with her love life. She was scared but she was also ready to meet “that special someone.” She joined a Meet Up hiking club because she loved to hike, and very soon after met someone she really liked. They started dating nearly immediately. It became a serious relationship pretty fast!

Honestly, I was astounded how my go-to single friend became part of a couple so quickly! When I asked her about this she told me it was because they were both ready and knew what they wanted. In her case, her age helped. After six decades on the planet she knew what she wanted. When she found the right person she did not take them for granted. She nurtured and fostered the relationship and it very quickly blossomed.

Second, attitude and intention are key.

Andrea was not ready to start dating until she was done with her grieving process around her ex-partner. But when she was ready, she put herself in alignment with her intention and actively put herself out there. She told the world through her actions: “I’m here and I’m ready to meet that special someone.” I think because she was so clearly aligned with her intention to meet that someone special there were few obstacles and it simply flowed.

My other friend, Martha*, was not so clearly aligned with her intention as Andrea. She was lonely but she also had self-esteem issues and didn’t like her body. She was afraid to put herself out there. She complained that she was too old, too fat, too…. And the list went on!

Martha had some work to do around shifting her attitude. She decided to join a gym, found a trainer she liked, and started getting her body back in shape. She also paid closer attention to what she was feeding herself. She cut back on alcohol and comfort foods. She went back into therapy to address her fear of rejection. Pretty soon she started to feel better about herself and more confident. She decided to try online dating. She put a picture and a profile on a dating site for 50+ people called She’s now dating and having a blast!

Martha tells me: “You have to appreciate your body or at least be pretty comfortable with it; otherwise you can’t relax and enjoy sex.” She is a good example of someone who put some effort into shifting her attitude about herself, and it paid off. She tells me that when she is with her lover she feels like a teenager again. When I see her these days she is so vibrant and alive, she positively glows!

“Why is dating so hard?” – Women in Transition + Obstacles to Dating Effectively

I work with a lot of women who are in transition, either starting or leaving an important job or relationship. During transition times attitude is extremely important, and a strong, positive attitude can really help. However, so often this is not what women experience during transitions; instead, old traumas and big fears surface. I bring this up because so often traumas and fears can completely derail mature women getting ready to date. If this happens, it is important to find a professional well versed in working with trauma to help, because trauma does not go away by ignoring it.

The good news is that if old traumas and big fears do surface, this provides an opportunity to clear them out once and for all. This is such an important first step before a woman can really get in alignment with her intention and move forward towards what she wants.

Another big obstacle to dating happily and effectively is a scarcity mentality. This is the belief that there are a finite number of suitable people for you and they are all taken! Moving into an abundance mentality is key to being able to date effectively. This is a state of being in your power and aligned with your intention and purpose so that what you need and want can flow towards you. Andrea, Martha, and numerous clients, as well as my own experience, have shown me that this mindset of abundance is key to a successful dating experience.

My friend Martha is an example of someone who had to do some work to get back in her power. She did this by tackling her self-esteem issues and shifting her fears around rejection. Once she felt better about herself she was able to define more clearly what she wanted in a partner, and she was more able to feel like she deserved that someone special. Martha told me that this is what she likes about online dating. “All the power is in the women’s hands—we get to pick!” Now there is a woman in her power!

For Martha, clearing out her own obstacles and fears also opened the door to getting more in alignment with what her intentions were with regards to dating. All these preliminary steps helped shift Martha into that abundance mentality so important for dating. Indeed, when she finally got her online dating profile out there she received an abundance of responses! She was able to have fun with the dating because she felt good about herself, and she was able to navigate effectively through a few “frogs” because she was clear about what she was looking for in a partner.

In closing, I hope Martha’s and Andrea’s stories and my own reflections have helped clear out some fears and provide direction if you or a loved one is battling fears about dating later in life. Working with yourself to clear out obstacles and old traumas, getting in alignment with your intention for dating, being in your power, and shifting from a scarcity mentality to a mindset of abundance will all ensure that you can not only navigate dating more effectively but maybe even have fun with it! Enjoy… : )

*Names changed to protect confidentiality.

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