Why Can’t I Find Love Again? The Challenges of Dating Over 40

Questioning why can’t I find love again? Looking for love comes with it’s own unique challenges over 40. Discover how to overcome them and meet your mate.

why cant I find love againWhy Is Dating So Hard?

Have you been looking for love for a while now and feel unhappy with your results? What can be more frustrating than hoping to meet the man of your dreams and coming up empty handed?

Time is slipping by and you are still not meeting the right man. Why is this happening to you? Why should it be so difficult to connect with one decent guy? And most importantly, what can you do to turn things around?

I’ve been in your shoes and understand the pain you feel. When you have been single for too long, it leaves you wondering how you will ever be able to change your status. You struggle and fear nothing will make a difference.

It’s hard to imagine what could happen that will change the course of your love life. Who knows what will help you finally connect with that one amazing man you’ve been dreaming about for years?

Why Can’t I Find Love Again?

There are so many reasons why love might feel illusive. I put them into four categories:

1. Lack of Activity. If you do something only once a month or less, you are not actively seeking love. You may be thinking about it but, you need to take action weekly if you are serious about meeting you mate.

2. Low Self-Esteem. You don’t feel worthy of love. When you lack confidence, you attract men who do not appreciate you. This is because you don’t appreciate yourself or understand your unique value as a woman.

3. Anger about Men. After being heartbroken, cheated on, or disappointed, you have a bad taste in your mouth about men. You might feel most men are not good enough for you or that in general women are superior. This makes it nearly impossible to find a man who can jump the unrealistic bar you set.

4. Dating Knowledge. Last but not least, some women hold mistaken ideas about dating without realizing it. This can be the hardest situation because you don’t know what you don’t know. So you could be making devastating mistakes with the best of intentions.

Do you see yourself in any of these categories? Maybe more than one applies. It’s not surprising because these reasons are commonplace and many women suffer from a mix of reasons, leaving them asking, “Why can’t I find love?

What Can I Do to Turn Things Around?

The good news is there are a number of empowering steps you can take to get past these limitations that prevent you from meeting “The One”. After going through this myself and meeting the adorable man I married, and now being a dating coach for women for 16 years, I have a pretty good idea. Here are 10 empowering steps you can take to change your romantic karma once and for all to find love again.

10 Steps to Find Love Again

1) Clear the Past. If you want to find love with a good man, you have to be free from your past. You want to clear a space for your new man. This means toss old love letters and other mementos, get over the anger about your situation or your ex, and find a way forgive your ex and yourself!

Don’t skip this step -it’s really the most important. When you look for love without clearing feelings about your ex, it will be very difficult to connect with a new man at the heart level. In fact, you might attract men with similar issues which happens often for many women.

2) Believe in Love Fiercely. One thing that helps attract love into your life is a fierce belief in love. Develop a deep knowing within that love is your destiny. At this point, even though there is no evidence, you have no doubt of this truth. This belief gives you a foundation of strength to weather any storm or disappointment along the way.

Coming back to this idea kept me going wile I was dating to find my husband.

3) Love Yourself Deeply.  You know you are a great catch and you have an appreciation for who you are as a person and a woman. Self love provides solid footing for surviving rejection and establishing firm boundaries. When you feel worthy, you’re able to draw the line and not accept anything less than being well-treated.

4) Learn What Works Online. If you are using the dating sites or dating apps, you are taking the steps needed to meet new men. Dating is a sorting process to find a good match and you have to meet men to find “The One.” But knowing what works on these digital tools is not so obvious.

Discover what works by reading a book, taking a class or signing up with a coach (like me!) If you don’t, you are likely doing things that are getting in your way of success.

5) Meet 3-4 Men a Month. When you are serious about finding love again with the right man, you make yourself available to meet men. Your dream man can’t find you unless you are out and meeting men! Make his search easier by doing what is needed to have 3-4 first dates a month and you are on the path to finding love.

If you often ask yourself why can’t I find love again, it might be because you don’t meet enough men. No excuses – get out there!

6) Be a Fun Date! Are you a fun date or is your first date a fact-finding mission? If you tend to do detective work by texting, talking on the phone or interviewing your date the first time you meet, YOU ARE NOT FUN! Keep in mind he is checking you out too and you have to pass HIS test.

You will learn what you need to know with time, so do not ask why he got divorced right away. That will make him uncomfortable. Give a man time – you can share your love war stories later as you get to know each other. And if you ask before some trust has built, he will not answer truthfully anyway.

Keep the date fun, light and entertaining if you hope for a second date.

7) Keep Expectations in Check. Dating can be very exciting when you meet a man you like who seems to like you. However, you need to manage your enthusiasm because you can literally scare him away by expressing your excitement too soon.

Share your enthusiasm with a girlfriend, but be cool with your new man. Smart women play their cards close to the vest and let a man express himself first.

8) Roll with Rejection. When dating, rejection is bound to happen. You simply can’t avoid it because there will be men you don’t like and men who do not like you.  Managing your expectations better, you’ll also handle rejection more easily. And, get back out there faster. You can become more adept at handling the disappointments so they don’t drag you down.

Don’t get stuck on why can’t I find love again and feeling down. Instead, roll with it and just go meet a new and better man!

9) Remain Optimistic. I help my clients find a way to stay optimistic about dating. Holding a fierce belief in love being your destiny can keep you moving and feeling more positive. And when you feel positive you are so much MORE ATTRACTIVE to men! There are always new men to meet to chin up.

10. Persevere! If you are serious about having love in your life, you need to keep dating and meeting men until you find “The One.” When I was looking for love, my ability to stay the course kept my search active. When I wondered, “Why can’t I find love again?” I’d shift my thinking to the idea that he was on his way and I would just keep meeting men till I found the right one for me.

There’s no question that dating over 40 and in midlife and later is more challenging than when you are young. But I say, so what? If you want love, DO WHAT IT TAKES TO FIND IT! My matchmaker friend Nicole LeClerc from Compatibles in VT said, “No one ever looked back after finding love to say, “Oh what a waste of time that was.”

No way! You’ll know it was worth every crummy, disappointing date you had once you find that one amazing man who loves you dearly. The guy who is fun, supportive, generous of heart, and willing to share life’s up and downs. A man who is sexy, sweet and enriches your life.

He’s out there so help him find you!

If you want more dating advice for over 40 or any age, download my free book 7 Dire Dating Mistakes that Keep You Single


Single for too long, Ronnie wanted to find love. So, she made a few tweaks and then dated 30 men in 15 months to meet her adorable husband Paul. Discovering the keys to midlife dating, she founded It’s Never Too Late for Love to help other smart, successful women find love too! Her mission is to share her proven dating advice  and keen insights about men with women everywhere who are serious about finding love with the right man. Ronnie Ann Ryan, MBA, CCC is a Certified Coach who has helped 1,000’s of midlife women with her Love & Dating Coach services. She’s been featured on BBC’s 5 Live Radio, NBC, ABC, and Fox News, NPR, eHarmony, MSN.com, MORE.com, Connecticut Magazine among others around the world. An established author, you can find her 6 books on Amazon.

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