Overcoming Challenges in the World of Online Dating for Professionals

I was 40 years old when my divorce was finalized and I began my dating journey all over again. Dating has never been “great” for me, but I wasn’t ready for the dating scene as a divorced single parent. It’s a whole different world for single adults in 2024.

These last 4 years in the dating game have taught me so many lessons. I’ve literally been studying single women as I go through the dating process. I’ve learned that despite what people say, I believe most single women (30s-40s) are not rushing into a committed dating relationship, as they view it almost like a form of emotional slavery. So, men wanting to date need to be patient and open-minded.

I’ve dated at least 50 women in the past 4 years. (I physically met these women, and we went on a date. Probably 80% of these women were one-and-done’s.)

In the past 4 years I’ve pursued around 200-300 women on online dating apps and social groups. (These are women I’ve matched with and connected with outside the dating app. We’ve texted and called, flirted, etc.)

I’ve experienced it all. I’ve been ghosted, catfished, disrespected, ignored, lied to, rejected, kissed, hugged, manipulated, shacked up, criticized, demeaned, took women on expensive dates, introduced women to my friends/family, etc. I even traveled internationally to a single’s event. I paid for a matchmaker. I’ve attended church single’s conferences. I tried dating long-distance. I even broke my own dealbreakers and went on dates with overweight women 🙂 .

After reflecting on my dating experiences, I feel my opinions on dating are just as qualified as any relationship counselor, psychologist, or therapist.


Why Is Dating So Difficult For Single Professionals?

Dating is so difficult because there are so many complexities involved in creating and maintaining a new relationship. Most of us lead busy lifestyles and prioritize our careers over our relationships. Plus, we all can be egotistical, stubborn, prideful, selfish, and impatient at times.

In order for single adults to have hope and remain positive, we have to constantly remind ourselves that NOT ALL women are selfish gold-diggers, and NOT ALL men are sex-crazed narcissists.

If you listen to social media, you’ve probably heard someone say, “All single women over 35 will never find true love.” Or, “All men under 6 feet who earn less than $100K/year will never find a wife.” Those statements may be true for some, but it’s not true for everyone. The truth is… true love can exist for anyone. The question is, are people willing to make the necessary sacrifices to obtain love?


How Do I Meet Someone Special?

When I was attending single’s events, so many women asked me, “Jason, where are all the single men? What do single men do?”

Their question made me realize the number of single women who don’t have a sincere friendship with single men they respect (or are attracted to). My answer was always… “Most single men (who aren’t gay) don’t move through life like single women. It isn’t normal for us to casually socialize in groups… unless it’s a work event or a sporting event. We are either somewhere working on something, enjoying family, pursuing another woman, or at home resting.

In my opinion, the best way to meet someone special is to put yourself out there on the dating marketplace. Let people know you’re single and available. Learn a new talent. Visit a new church. Make new friends and get out of your comfort zone. There is no special place to meet someone special.


How Do I Know When I’ve Found Someone Special?

Do not be afraid to ask questions! Some of the biggest relationship mistakes I’ve made were because of assumptions I made. Now, I’m very inquisitive when I meet a single woman. I want to know where she lives, if she has a car, does she have a criminal record, where she works, what does she want in a relationship, when was her last sexual partner, does another man thinks he’s in a relationship with her, etc.

I could write a book about this, but I believe there are 10 deciding factors which will ultimately determine if someone is worth dating. There has to be some form of compatibility in all these areas.

1. Age – (maturity, life experience, generational norms) – There are more single adults in their 40s-60s who dress, act, and live like they are in their 20s. Age matters, despite what anyone says. It matters the most when it comes to nonverbal communication, parenting, and social life. I try not to date women who are either too young or too old to relate with socially.

2. Children/Family/Friends – (responsibilities, character traits) – As a single father, I honestly prefer to date single mothers, because we automatically have something in common. Also, there are so many single professionals who have little to no close relationships. To me, that is a red flag. People without any close relationships with friends/family generally have trust issues or experienced some sort of emotional trauma and need therapy.

3. Emotional Availability – (previous dating relationships, busy careers) – Do not ever assume you know what someone has been through in their previous relationships. Personality and communication style are very important when dating, as we all need to feel like we’re understood. There are also a lot of people who chose careers that drain them emotionally, so they have literally nothing to offer emotionally in a relationship.

4. Financial Stability – (maturity, intelligence, work ethic) – Having a stable income and living within your financial means is one of the most respectable qualities a single adult can have. The amount of money a person makes and how they manage it is important.

5. Health – (life discipline) – No single adult is signing up to be an unpaid nurse (unless they’re rich). Exercising and being healthy is very attractive. How a person manages their body will show you how they care for the things most important to them.

6. Lifestyle Priorities – A healthy dating relationship is where both people live compatible lifestyles. If you date someone who doesn’t share or respect your values (religious beliefs, family values, cultural norms) there will ultimately be confusion and disagreements.

7. Location – (accessible, available) – With all the catfishing going on within dating apps and social media, it’s imperative to date someone who you can causally and easily spend time with. I’ve tried long-distance dating relationships. They may work for a select few, but they are not realistic for the average single adult looking for a meaningful healthy relationship.

8. Love Language – (communication, sexual intimacy) – I read the book 5 Love Languages. I believe it’s very important to know what makes you feel loved and how you naturally express love. It’s easier to date someone who shares a similar love language.

9. Physical Attraction – I need to be physically attracted to any woman I’m pursuing. No one is perfect, but I would never date someone who I wasn’t attracted to.

10. Relationship Goals – (intentions, values) – It’s so many reasons why people are dating. Do not assume someone is interested in you because you’re special. It’s a lot of people who are dating only because they need money, or they need help moving, or they want a friend, or they want to feel validated emotionally, or they want their sexual needs met.


I’m not always right… but I’m not always wrong either. Date wisely.

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