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Jul 22, 2025Dating Confidently After 40-Flaws and All – Dating Relationship Coaching & Advice
- Jul 22, 2025
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Dating after 40 can be challenging for both men and women. It is especially tough if you have been out of the dating scene for many years.
I have spoken to numerous women who are insecure about dating in midlife, due to the changes in their appearance. They have little voices inside their head that sabotage their efforts to date, because they don’t feel attractive. “I’ve gained weight, I’ve got wrinkles, men are only interested in hot, younger women.” Many men also experience these insecurities, but they don’t often express them openly.
My male clients have told me that they are attracted to women who are proud of their bodies. They appreciate women who are comfortable in their own skin, regardless of age or size. Confidence is an attractive trait that shows your authentic self. This is refreshing to see in the dating arena and makes a great first impression!
You have earned your body transformations over the years, OWN THEM!
You may not be 25 anymore, but you’re wiser and far more self-aware after 40. Not only that, but you also have more clarity on what is important to you in your friendships, your career and a future partnership. You achieved wisdom from growing through the trials and tribulations of life over the years. Appreciating and embracing every phase and new decade is imperative for personal evolution.
Photo by Nataliya Vaitkevich
We all face challenges and carry emotional scarring that can keep us stuck.
It is difficult to get through life without navigating through some big obstacles. Emotional scarring from past breakups and dating scenarios is one of these issues. The most valuable thing to take note of is that you implemented change when something didn’t serve you well. You also understand what it means to love someone and to be loved back.
There is now a better understanding of how to deal with new complications that arise in your life. This is a wonderful thing! You are progressing and appreciating each new path you venture out on. You acknowledge the lessons you had to learn at the time, trusting that each one holds a purpose in shaping who you’re becoming.
Photo by Vlada Karpovich
Showing gratitude for all your experiences guides you to a better place each time.
Understanding those important lessons is half the battle to living your best life. Dating at an older age will definitely have challenges, but there are also many advantages. With age comes wisdom and a powerful learning tool! Whenever you’re giving yourself a hard time about your appearance, look around at the people you admire. Are they flawless? Are they the perfect size 6? I would bet not.
The aspect that stands out most for both sexes is how they present themselves on a daily basis. When someone is personable, kind, funny and truly comfortable with who they are, they have a receptive presence! Someone who has lived life with enthusiasm and confidence is attractive, regardless of their physical appearance!
I find myself drawn to older people who have a zest for life and a big smile on their faces. Grandparents are stepping up and having more fun. We are starting to see this more frequently on YouTube and TikTok, social media sites. Mature men and women are not allowing themselves to get stuck in a stereotypical aging pattern.
When you’re open and playful regardless of age, you’re not being pretentious or fake. You are being real! There is an understanding that having an outgoing personality is even more alluring than being cosmetically flawless.
How do you go about feeling more confident when dating?
#1 – First impressions are lasting impressions.
Discover a personal style that highlights your best features and showcases your unique personality. Many YouTube channels offer this exact thing. There are numerous fashionable clothing styles available for mature men and women.
If you’re not sure how to proceed when out shopping, ask a clerk in the store for assistance. They can help you find a fashion style that brings out your best qualities. Don’t be afraid to try on something that might be out of your comfort zone. Sometimes we need another pair of eyes to see what we may be missing. Get rid of anything that screams frumpy in your closet! This goes for both sexes. Women love men who know how to dress well!
Attitude is another thing to pay close attention to. Say hello to people you pass on the street, at a shopping mall, or your fitness facility. Up your friendliness to attract other people toward you. Smiling is contagious! Happy people bring happiness to their lives.
#2 – A new hairstyle and adding a fitness regime to your life will help you gain confidence to feel more attractive.
Find a youthful style that you love and complements your face. Just because you’re 40-plus doesn’t mean you have to cut your hair because you think certain styles aren’t age-appropriate. Do what makes you happy and forget about any archaic beliefs.
If you are struggling with weight gain or health issues, it is very important to include a daily fitness routine. Get yourself a step tracker and work up to doing 10,000+ steps per day. I use a device called a fitbit and push myself to get my steps in every day. Yoga is a great way to stay fit and also lift your spirits at the same time. I have always said that exercise is an inexpensive form of therapy!
There are also some great ideas for lowering your food consumption as well. Intermittent fasting is a great plan and still allows you to eat some of your favourite foods. I do the 16-8 ratio whenever possible. I fast for 16 hours and only eat in the 8-hour window. It helps you to maintain your desired weight. The keto diet is also a great way to reduce excess weight, but some people have a difficult time omitting carbs from their daily menu.
#3 – Do not use negative dialogue discussing your insecurities.
Be cognisant of this, especially when you’re out on a date. It will not be your flaws that prevent you from getting that second date; it will be your lack of confidence and self-appreciation. We all have insecurities, but we shouldn’t go around continually talking about them. Some people aren’t even aware that they sabotage their dating life by doing this.
Reverse the situation to think about how you would feel if someone were talking badly about themselves. I can assure you that it would be a turn-off. Having self-respect is very important!
#4 – Be mindful of self-deprecating behaviour.
Criticizing your appearance or lamenting over what’s not happening in your life is harmful. It’s a very bad habit to develop. Be mindful of talking negatively about yourself, to yourself. Even just thinking in a pessimistic tone will keep you stuck in an unhealthy place. Everyone has good qualities; choose to focus on those. This will dramatically change your life. Positive thinking really does bring more positivity toward you.
#5 – Hang around with optimistic friends and family.
If you find that some of the people in your life are in a pessimistic state of mind, remove yourself from their presence. Behaviour breeds behaviour, and if you are spending a lot of time with negative friends, it will eventually start to rub off on you.
Optimistic people look at life challenges as opportunities. They are quick to problem-solve when things become difficult and don’t get stuck in victim mode. This type of friendship celebrates your successes and helps you find the silver lining when you are struggling with certain things. Their positive reinforcement is contagious, which gives you motivation and hope.
Conclusion
Dating after 40 isn’t about perfection; it’s about authenticity. It’s about being real and showing up as you are, with all the lessons, laughter lines and life experience that make you uniquely attractive. It’s about owning your story, quirks and all! This refreshing attitude helps you create space for real connections that see past surface judgments.
Walk into this next chapter knowing that the right person will accept your imperfections and appreciate who you are and how you got to this place in your life. Confidence is sexy, and life experience is priceless.
Anyone who can’t handle your fabulous flaws isn’t the right person for you. It takes time to learn how to deal with the changes as you age, especially when you have been single for a long time. It is a work in progress for sure. Confidence doesn’t come from erasing your flaws; it comes from owning them!
*Please watch the video below for more information on today’s topic
Thank you, Sybersue xo ❤
Private Dating Relationship Coaching With Sybersue—Please don’t hesitate to contact me at [email protected] and message me there to set up a video or audio appointment within 24 hours. Thank you!
Susan McCord @ Dear Sybersue YouTube – Dear Sybersue Facebook
Dear Sybersue Blogs & Advice Column – Dear Sybersue Instagram
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