Who Else Wants To Enjoy DATING OVER 40

"This might seem harsh, but you are likely telling yourself several lies about love after 40 that are hurting you. These negative beliefs prevent you from connecting, or worse, stop you from even looking."
An interracial couple dating over 40 face-to-face looking at each other

Finding love in your 40’s can be a challenge. It’s something I’ve heard but didn’t believe it until I started to think about the possibility of allowing myself to love again.

After many failed relationships, it’s not something I thought I would ever want again. Plus, when you’re Ex is your best friend, it’s easy to escape the idea of dating. It’s like having a boyfriend without sex.

Funny, does anyone date anymore? Although I’ve not put myself in a position to be asked out on a date, it’s laborious to imagine a guy, especially a gay guy who is romantic, or interested enough to ask someone on a date. Even when I read my previous statement, I want to cringe; it sounds cynical and negative. I do know that you have to be willing, open, and positive about love for it to find you.

Now, let’s face it; when you’re over 40-years old, dating is not so much a challenge, it’s superficial. It also takes a lot of patience, but most importantly, self-awareness and self-confidence are the two things that make dating easier. When you’re confident in who you are, you begin to date with purpose, and as I used to say, “dating for success.” You begin to spend less time trying to impress someone, and more time trying to find out if the person you are with is a match for you. Plus, sex is great, and we all love it, but at a certain age, a healthy and long-lasting relationship can’t survive when sex is the sole foundation.

It’s additionally the reason why self-awareness is a person over 40’s best asset. They use magical power (maturity) to weed out the unlikely match reasonably quick and honest about it.

Rejection is hard, but truly it’s not when served with compassion, love, and understanding. The moment I know that it’s not something I want, I’m able to tell the person right away.

When I think about it, I haven’t been on a date in about 8 to 10 years. I’ve have had lots of fuck-buddies and long-term ones, but nothing that went beyond the bedroom. I was starting to think the fuck-buddy route was my only option, particularly at my age. I can’t dispute it; fuck buddy hookups are easier, but they sequentially become trivial and lack substance. The fuck-buddy phrase in some men’s lives stop working, their perspective changes, family, health, career, and traveling the world take over.

As we grow older, our list of what we want from a partner will change significantly. Instead of being caught up on looks, status, and the type of car someone drives, 40-something people want more. When you’re over 40, you fancy an individual who is kind, considerate, and who has a good sense of humor. Life teaches us that the inner substance is more valuable than outer flashiness.

Now, let’s get down to the real issue. Where the hell do you meet men or women seriously looking for a relationship?

What I noticed recently, including myself, during conversations with someone new, I’m quick to tell them what I don’t do, instead of sharing things about myself that I enjoy doing. It’s an instant turn off when you hear what someone doesn’t do.

In my case, I drink, love to hit a club once in a while, and love music. However, the other day, I was speaking with someone who I was crushing on, and during several points of the conversation, I heard everything he doesn’t do! Sadly, all the things he didn’t do were all the things I enjoyed, relationship buzzkill.

When you’re over 40, we usually have a different attitude towards relationships than younger individuals and more likely to be ready to commit because you know what they want in life, another benefit. Besides, we have more life experiences and will have developed strategies for dealing with problems and challenging emotions.

Even though I want to believe dating when you’re over 40 is a challenge, but the more I read my own words, I accept the truth, it’s me blocking the idea of love. We are fed so much mindful trash about dating that it keeps us from living and loving fearlessly. I still don’t know where to meet eligible men or women, but the more I think about it, that’s the least of my problems.

Having a positive state mind about love, being self-confident, self-aware, and open to the idea that you can find love at any age, it’s half the battle. The rest is a piece of cake. Your positive, self-assured attitude and confidence is the key to finding a date and potential the love of your life.

I wasn’t convinced I could find love at my age until I wrote this article, so I guess; this article was more about me! However, in the interim, I hope it helps you begin the path towards finding love.


Visionary Leader, Music and Hot Toddy Lover. After 15+ successful years in finance, I ventured out on my own, creating various brands, Flirtatious-T, Urban FLRT, Kinkster NYC, and now Milton Wes and OVAH MAG.