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As a woman who has lived through many passages and learned through my larger than life experiences (positive and negative), I’ve discovered how to take a big empowering bite out of life.

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Today’s story was written by Jacqui Baker, the CEO and founder of Select Connections, a dating agency for mature singles. She shares her expert advice on beginning to date as a woman over 50. Please read and enjoy, darlings!

mature dating coach in red standing in front of city

Jacqui Baker, CEO and Founder of Select Connections Dating Agency

As a dating mentor and fellow traveler on the dating-after-50 path, I understand the mix of excitement and apprehension that comes with being a woman entering the dating scene over 50. Let me share a bit about myself. I’m a 59-year-old single lady. About five years ago, life presented me with an opportunity for transformation as I found myself single once again. 

This led me to take bold steps — navigating the challenges of online dating and rediscovering my desires at this stage of life, which were quite different from the 1990s when I was last single. Let me tell you, the journey of dating as a woman over 50 holds potential for introspection, growth, connection, and an abundance of joy if you are open to it.

I bring you many tried-and-true tips based on my long-tenured role as a dating mentor.  Using the guidance included in this article, I encourage you to take steps to overcome your fear, embrace the process, and grasp a positive outlook as you embark on this new chapter of your life. 

Exploring Dating as a Woman over 50

As you start thinking about dating after 50, you will certainly experience a plethora of thoughts and feelings. Here are some of my top tips to help during this initial phase of the dating process.

Feel Your Feelings

It’s perfectly natural to experience a range of emotions when stepping into the dating world again. Excitement, nervousness, and even fear! All emotions are all valid when dating after 50. Give yourself permission to feel these emotions without judgement, and don’t hesitate to confide in a trusted friend or professional. 

Choose Self-Compassion

Ladies, be kind to yourselves. Remember, as a woman over 50,  you’ve navigated life’s many challenges and have a deep well of wisdom to draw upon. Though it is difficult, try to treat yourself with the same compassion you would offer a friend.

Identify Your Fears

We all have fears when taking on something new. Especially something as intimidating as dating after 50. When you feel the fear, slow-down, and take a moment to identify what exactly you’re afraid of. Are you worried about rejection? Or making the wrong choices? Are you nervous about getting hurt? Naming your fears can make them feel more manageable as you re-enter the dating scene after 50.

Challenge Negative Beliefs

Often, fear is rooted in negative beliefs about yourself. Take action to replace these thoughts with empowering and positive ones. For instance, replace the thought, “I’m too old for this” with “I have a lifetime of wisdom to share.” 

Take Baby Steps

Facing your fears doesn’t mean diving headfirst into the dating pool. Get your feet wet with small, manageable steps like joining social groups, attending events, or engaging in online discussions. Each step forward is a triumph. Setting goals in all areas of your life can bring success, the same is true as you being dating after 50.


Dating as a Woman over 50: Navigating a New Landscape

Once you have begun to date, you will encounter situations that require great communication and wisdom — two things that women of our age possess plenty of! As you dip your toes in the pool, remember to follow these tips.

Set Clear Intentions

How can you make decisions if you don’t know what you want? Ask yourself, “What am I looking for in a partner?” Try to define what you want in a potential relationship. This clarity will be a map for your decision-making and help you stay true to your goals.

Clear Communication

As in all relationships, open and honest communication is key! When you’re ready, speak up! Share your intentions and expectations with potential partners. This probably isn’t breaking news to you, wise one, but great communication is the strongest foundation in all relationships both old and new.

Learn from the Past

As a woman over 50, your sweet and sour life experiences have taught you valuable lessons. Don’t ignore the past. Rather, reflect on your previous relationships and identify patterns that you’d like to avoid or replicate in your future endeavors.

Open Your Mind to Dating as a Woman over 50

Yes, identify what qualities you want in a future partner, but also be open to meeting a diverse range of people. Sometimes, unexpected connections lead to the most beautiful relationships (both romantic and not).

Slow and Steady Wins

It can be difficult to move slowly as life rushes along. But I advise you to avoid rushing into a new relationship. Allow connections to develop naturally and give yourself the space to assess compatibility.

Lead with Positivity and Joy When Dating after 50

The experience of dating as a woman after 50 can be fun and exciting. Throughout the entire process, remember to implement these tips.

Feel Appreciation Always

Focus on the positive aspects of your journey. Each interaction, whether it leads to a partnership or not, offers a chance to learn and grow. Do what you can to feel grateful for every dating experience.

Celebrate Your Individuality

This is a fabulous time in your life to celebrate your unique qualities, especially the quirks that make you different. Pursue hobbies, interests, and passions that bring you joy and make you feel fulfilled. Honey recently shared some great ideas of hobbies to pickup after 50.

Lean into Your Support

As a woman entering the dating scene after 50, it is important to find support from your girlfriends or family. I recommend online support groups that understand and encourage your dating journey. Your network’s encouragement will uplift you during challenging moments. 

Stay Patient and Persistent

Finding a compatible partner can take time. Be patient. And trust that it will pay off. Remember, quality connections are worth the wait.


Being Single is Beautiful

For all the single women over 50 reading this, never feel like you must be in a relationship. Your intrinsic value is singular, and not tied to your relationship status.

Celebrate Personal Growth

Being single offers a unique opportunity to focus on yourself and your own growth. Perhaps you’ll rekindle your passions, hobbies, and interests that may have taken a back seat during other life phases, or maybe you’ll venture into new territory — Set goals, learn new skills, and explore new horizons.

Own Your Story

Being single isn’t a limitation; it’s a powerful chapter of your life story. Own it with pride, as your individuality is what makes you special. You’re not defined by your relationship status, but by the richness of your experiences. 

Fostering Connections

Being single doesn’t mean being isolated. Cultivate strong friendships and connections with friends and family, as these relationships can be just as impactful and fulfilling as romantic partnerships. 

Choosing Your Path

As you navigate the dating world, remind yourself that you’re not seeking a partner to “complete” you. You’re already whole! Any potential partner should complement the life you’ve built for yourself.

As you venture into the dating world as a woman over 50, remember that our journey is not defined by the destination of a full-time partner.  It’s defined by the experiences, connections, and personal growth we encounter along the way. We can choose to enjoy every phase of the dating journey. Whether we choose to remain single or to share our life with someone else, our story is ours to shape and celebrate.

So, when you step into the dating scene after 50, step in with the confidence that you are entering it as a whole and remarkable woman, ready to embrace all the fun and opportunities that come your way.




Head shot of mature woman drinking tea
Jacqui Baker is the CEO and founder of Select Connections. She’s a skilled dating coach with expertise in mid-life and later-in-life connections. Her mission is to provide a safe and supportive environment for her clients to explore the potential for love. Originally from Northern Ireland, Jacqui now resides in the picturesque countryside of the South of England. 

August 29, 2023

Passages After 50, Relationships

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  1. nancyD says:

    Great article… I’ve been on and off dating sites and really never have connected with anyone. Maybe my profile is too specific as to what I want or will not accept in a relationship. Also I’m in my early 70’s and the dating pool is slim…I just cancelled a renewal on a site because honestly, it’s not worth my time and money. Most men I find, just post a picture, if I’m lucky, and no narrative, or if they do, like me they are so specific, that I know they aren’t the one…maybe single is the way to go….but great thoughts to think about..

    • Susan Good says:

      Why not consider asking for what you want. “I am looking for a man who is…. End by asking: Are you the one! May work. It would be fun not to tell anything about yourself and ask him about himself. Let me know what you think? Warmly, Honey

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