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Dating 101: 5 Questions To Ask When Dating

Time is a finite resource. Nothing lasts forever. My time is one of my most valuable resources, so I’m generally very intentional on how/where I invest it, especially when it comes to dating.

I live my life with purpose. So I don’t want to waste my time and energy on dating a woman with different relationship goals. It’s not about wanting someone who agrees with me on everything, but wanting someone who lives a life that is in alignment with how I live mine.

7 out of 10 ‘single and looking’ Americans say their dating lives are not going well.

February 2022 Pew Research Center survey

Dating has evolved and is evolving. It will never be the same as it was prior to social media and dating apps. Studies show online dating is linked with mental health issues such as anxiety, depression and rejection.

The purpose of dating is to share your life with someone and grow together. You can’t expect someone to be your love, best friend, mentor, therapist, dating coach, breadwinner and sole support system.


Communication is so important in a relationship. I believe in addressing red flags and acknowledging deal breakers. So, I think it’s wise to be direct and ask questions. It’s unwise to make assumptions, nor do I date on potential. If I am interested in dating someone, I need to know…

Why Are You Single?

I need to know the reasons why an attractive woman is single. The reasons matter. It’s not because there aren’t enough available men. That’s a lie. There are a lot of beautiful women who are single because they have issues. They may have a toxic personality, bad attitude, controlling, egotistical, lazy, struggling financially or in debt… you name it.

The reason why someone is single will give you insight on who they are, how their relationship choices align with how they present themselves, and it may highlight any trauma they have been through.

Why Do You Want To Date?

Everyone has a different reason why they want to date. I would be naive to assume every woman who finds me attractive wants what I want. I find most single women want a relationship that serves their needs. Even Black-ish TV actress Tracee Ellis Ross said in a recent interview, “I would love a relationship that makes my life better than it is. I have no interest in just being in a relationship,”

I believe many adults have lost hope in finding real love. This hopeless attitude along with the fear of divorce has caused many singles to be negative or indifferent towards dating. So they have little or nothing to offer anyone because they have no real expectations.

Why Are You Attracted To Me?

Some may find this question difficult to answer. As they may not be intelligent enough to express their feelings verbally, or they could be unwilling to be vulnerable and transparent. I truly believe the reasons why someone is attracted to me holds lesser importance than the reasons why I’m attracted to them. Nevertheless, this question will give someone the opportunity to communicate their feelings. And, this question is a conversation starter; it will open the door to more questions.

What Type of Lifestyle Do You Live?

More people are getting divorced due to irreconcilable differences and lifestyle preferences. I’ve dated women who loved me as a person, but when she found out some of my close friends were white or were Republican, she quickly dismissed me. If I knew she was a closet racist in the beginning, then we would have never dated, and I would’ve saved a lot of time & money 🙂 .

In all seriousness, a person’s lifestyle will dictate what they invest their time into and the things they value the most. Understanding how someone invests their time can ultimately tell you if they are in a position to put energy into a new relationship. Quality time is one of my love languages, so knowing a woman’s lifestyle is very important, as I will not date someone who is already married to their career or their personal hobbies.

What Does Family Mean To You? Are You Open To Having Children?

No person can create a family or create a child alone… God made it so that it takes two people to create a family and a child. This is a deal breaker question for me. It’s all about compatibility. As my desire to have a family and children are the top reasons why I even consider dating. So, every woman I date has share my same love for family and children.

Compatibility is important especially if you are open to dating outside of your race or someone from a different culture, as everyone has different experiences and things they prioritize.

So many people today have different upbringings and do not know what they want out of a relationship. Except, they know they want something custom fit for them. Two things which amaze me the most about dating are: (1) the amount of women who want a committed relationship, but don’t want to get married. And, (2) the amount of single Christian women who want to be married, but do not want children.

I hope this blog helps someone find the person they’re looking for. Be positive. Stay encouraged. Love isn’t something you find, love is like a seed, it is sown and reaped.

svg7 min read

Jason Perry

I'm a black man with Christian values. A father to my son, a friend to those who desire my friendship, a lover of life and even more...

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This is my journal, my journey, and my perspective in life – JP
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