Alright! So, this is the first of two posts detailing the top six ladies I met through Online Dating Sites and how I failed spectacularly. Spoiler alert, with some of them, I admit I may have been the problem. I’ll let you be the judge.
Points Discussed
- Cassandra: The Girl Who Bragged about Being Difficult
- Sydney: The Christian Who Has Gay Friends
- When Single Moms Raise Children to Take the Place of Their Spouses
- Aleah – The Feminist Christian
- When the Woman is More Masculine Than You:
- Patricia – The Girl Who Was “Too” Christian?
Cassandra: The Girl Who Bragged about Being Difficult
First up, we have Cassandra! She was the first match I ever got from Online Dating Apps where I got a girl’s phone number and we actually went out on a date. This was in September 2014. I had just turned 28-years old.
Cassandra or Cassie was a 25-year-old social services case manager. White girl, slender, fairly plain in appearance, but pretty enough for me to entertain the possibilities. And of course, the thing that set her apart from others was the fact that she responded to me and our conversations were good.
I remember one of the things she kept saying she liked about me was that I reminder her of “Rhett Butler”. lol, I wouldn’t find out until years later who that was.
Around that time, I was still a novice in my Christianity. I had just begun my first read-through of the Bible earlier that year, so I was looking for someone who was also faith-based. Cassandra claimed that she was on her profile.
Brief aside…but you can tell a lot about a person based on their favorite music, TV shows, and whatever they’re a huge fan of. I’m not saying they’re red flags or deal breakers, just things to be mindful of. With Cassandra…she obsessed over a TV show called, “Big Bang Theory”. Hahaha! Hear my out.
The problem with shows like Big Bang Theory and Glee was that they were ridiculously unrealistic. I didn’t believe for one second that those nerds would be able to pull hot girlfriends like the ones you saw on the show.
More than that, I saw how these shows changed the masculinity of my generation. Gone were the days of the 90s kid, where we grew up with role models like Michael Jordan, seeking competition, pursuing dominance, and carrying yourself with confidence. All this might be considered toxic and undesirable to fans of Big Bang Theory and Glee.
Whereas…the shy, quirky, self-deprecation of Soy Boys became more popular with the white 20-something females who were also left-leaning and big into female empowerment.
Leading me to her claims of being a Christian. Far be it from me to say she wasn’t. I was still a beginner myself at the time…but I recall one of the first things she told me.
When I got Cassandra’s number and we started talking, before we even made plans for our first date, she warned me that she was difficult…difficult…
Now, some of you might be thinking, “difficult as in, difficult to get in her pants?”
No. Cassie bragged that she was just difficult to cooperate with. And, inexperienced 28-year-old me didn’t see that as a problem.
When men complain about women nagging them or always telling them what to do…I wasn’t fazed by that. A woman can nag and tell me what to do all she wants. Doesn’t mean I’ll actually do it. And as long as she doesn’t put her hands on me, I was good.
Nah son…Cassandra proved how difficult she was when it came to planning the first (and only) date. First it was the location, which was a scenic park in New Port Richey. Then it was “where do we park?” I offered suggestions, and she shot them all down citing some frivolous concern.
When I encouraged her to make a suggestion, she’d turn it around on me and say “she expected me to take charge and make the plans.” That took up a lot of time when I should have been working that night.
When we finally got to the date, it also happens to coincide with a biker rally in that park…the date itself wasn’t bad. I had a good time just chilling and talking with her about this, that, and the other.
After 4 hours of hanging out in the park, I walked her to her car, kissed her goodnight and sent her on her way. A few days later, I called and started talking about when we’ll see each other again. She said she was available on Sunday but gave me an answer of, “we’ll see.”
When I pressed her for a yes or no, she said, “How about you stop pressuring me and take the answer I give you!”
That’s when I said, “Alright, I’m done. You were right. You are too difficult. I should’ve listened. This is on me.”
She said good-bye and that was it. I’ll tell you what wasn’t difficult… Getting over her.
That, and the fact that she didn’t want children because, as a case worker, she’d rather help out and adopt the children who lacked families than bring her own child in this world. That sounds noble…but also, in my opinion, a bit selfish, solipsistic, and un-Christian like.
Meaning, it’d be one thing if you were barren or you’re simply incapable of producing children. But as a Christian, there are plenty of Scriptures supporting the ideology that we were put on earth to reproduce. Women were created to be a helpmate for men. So, unless you find a man who also has the goal of adopting children with no desire to father his own, you’re basically requiring that man to forget his own goals to put yours first.
I really should go deeper about that, because I can see how that might be controversial. I’ve seen some “Christian” women aggressively argue against the notion that if they’re not with a man or don’t have families and children then something’s wrong with the woman.
And to be clear, I wouldn’t say “there’s something wrong with them”…at the same time, I do think there’s a lot of coping going on. But let’s continue.
Sydney: The Christian Who Has Gay Friends
Sydney is perhaps the one where I was too hasty, inexperienced, and I may have dropped the ball. Because she wasn’t a bad person. I was just too quick to pass.
After dealing with Cassandra in 2014, I stepped away and swore off dating sites for seven years, until September 2021 when I signed up for Match.com. I was 35-years-old.
Sydney was the very first girl I “matched” with and even befriended on Facebook. Here, we had a beautiful black 26-year-old surgeon based in the Orlando area. She was smoking hot and had a lot going for her. Yes, she did have a chest tattoo like this AI generated image shows.
I was a little disappointed that she lived in the Orlando area and was confused as to why she’d want me. You’d think it’d be easier for her to get any man she wanted a little closer to home. Either way, we struck up conversations with some fun-spirited discussions.
By this time, I was a full-committed Christian. I had already read the entire Bible once and was determined to live my life according to those principles, so I was hoping to find a woman who also strives to do the same.
Sydney claimed she was a Christian and respected my willingness to wait until marriage to have sex. Spoiler alert, they always “claim” this.
After talking to Sydney for over a week, it came time for us to exchange numbers. I confess, I was still a bit dubious about her being in the Orlando area and whether or not I was being scammed or cat-fished.
So…I put this question to her, “If the Bible says that such and such is an abomination, but the world says it’s acceptable and even has a parade for it, which way do you sway?”
Her response was, “I have gay friends and I don’t feel the need to shove my beliefs down their throats. You seem a little too conservative for me, so I don’t think it’s going to work out.”
I respond with, “You’re right. It’s all good.”
I could’ve fought for her. I could’ve schooled her and gone into depths about what the Bible says on the matter. I could have revealed the Scriptures of 1 Corinthians 6:9-11 or Leviticus 18:22 that explains how God feels about the matter and if you “put God first” then you’d value what He thinks over what humans think.
But she was the first girl I matched with and I’d only been on the site for about 2 weeks. Thus, the urgency and desperation weren’t there because I was sure I’d find someone else just as quickly.
In studying Sydney’s Facebook behavior over the years, I don’t have any regrets.
From what I saw, she has a lot of the hallmarks associated with stereotypical Black Women. Wanting to wear the pants in the relationships. Prioritizing her career, degrees. Becoming a homeowner and having her Single Mom constantly around. This doesn’t make her a bad person! I just don’t think our goals are aligned.
When Single Moms Raise Children to Take the Place of Their Spouses
Having her single mother as her best friend is not necessarily a bad thing. Trust me when I say, I’ve seen accounts of possessive boyfriends coming in and refusing to let their girlfriends talk to their friends and family. That’s a huge red flag and women should leave those guys alone.
That being said, when it comes to dating a woman, I have no desire to be a provider for her mom, her pets, her siblings or any other symbiotic relationship she’s chosen to take on as a dependent. Especially not in the beginning of the marriage.
Some men can do that. God bless them. But I’m not that guy. I tried to be that guy when I was 27. Back then, I dated a single mom who’s daughter was in 2nd grade, she owned a dilapidated home, and her father lived in one of the rooms. That was a lot to take on.
And it wasn’t until Sydney that I started seeing a trend of how a lot of Single Mothers train their children not to branch out start their own families. Instead, they’re being groomed to continue serving and taking care of that Single Mother forever. It was just by chance that I revisited this video by Kevin Samuels who broke it down with plenty of women admitting that this is exactly what’s happening.
These are the types of Single Mothers who often inject themselves in their daughter’s relationships, not in a healthy way…but to make sure no one else takes her place of importance or priority in her daughter’s life. Meaning, “If you date my daughter, remember that you will always come in 2nd place to me. My happiness is more important than yours when it comes to my daughter.”
I’m not saying, “if the parent falls on hard times, you shouldn’t step in to help out.” That’s not what I’m saying at all.
What I am saying, is that it seems a lot of Single Mothers believe their children were put on earth to serve and prioritize them no matter how old they get, and regardless if they get married and have their own children. Whereas, my parents raised me and my brothers to get up out of the house, be self-sufficient, and start our own families.
It’s not just women who are being groomed to think this way. But I’ve seen clips where men will demand that their wives sit in the literal backseat and argue that their mother will always come first. (although, some cases are due to a fear of gold-diggers)
This reel has a group of men being asked who comes first, wife, daughter, or mom. And a lot of men chose their daughters and moms over their wives. The female host, clearly had a problem with it.
“So! What’s wrong with that, Rock! She raised you! Who are you to judge those people if they choose to make their mothers the center of the universe regardless of getting married or having they own kids!?”
Good point. The cool thing about being a Christian is that we can rely on God to answer such monumental questions. In Matthew 19:5-6, Jesus Christ himself said that Man will leave the mother and father to be united with his wife. What God has brought together, let no one separate. All this goes to show how far we’ve moved away from how God calls us to live, and clearly, men are guilty of it as well.
You can still honor your mother and father. But when you get married, your spouse takes priority. That being said…ladies, you should know that if you’re wanting to marry a Christian man who believes in protecting and providing for his family, it would behoove you to eliminate obstacles and detach yourself from things that would put added pressure on his burden to provide.
Because if he’s like me (honest, observant, and values his peace), it doesn’t matter how hot you are or how much our personalities click, we’ll likely exclude ourselves from dating you because we’ll assume we’re just not enough to take care of you and everything that comes with you. It’s “too much responsibility”.
No lie, even with my current fiancée, soon to be wife, we’ve had plenty of talks about this. From the get-go, I’ve made it clear that my focus and priority will always be on the family we hope to build. I didn’t sacrifice and work hard for over a decade to throw it all away on someone else’s poor decisions. As cold as that sounds, it’s the truth that a lot of men are too afraid to admit. Instead, they’ll simply ghost you to avoid those uncomfortable conversations.
Aleah – The Feminist Christian
Ah, Aleah, hahaha! In October 2021, Aleah was another lovely 26-year-old medical student based in the Charlotte, North Carolina area. She’s the one who prompted me to write an essay called, “The Truth about Wives Submitting to Husbands, Christians who Reject Parts of the Bible.”
Again, it was concerning that yet another lady was trying to date me from long distance. It was depressing that no one in my city matched with me, leading me to believe I was just living in the worse location. I may be an 8 in Atlanta, but in Tampa where everyone’s a beach, athletic dude…I might be a 4.
Thus…when it came time to exchange numbers with Aleah, I think I was more open to it than when I was with Sydney.
Aleah purported herself to be a Christian. She comes from a healthy two-parent household, of black Caribbean descent. She even sent me pics of the family attending a Panthers football game. It was nice.
The problems with Aleah started when I called her over the phone. On paper, we matched. But those phone calls were critical because we were long-distance. I’m not taking the drive out to NC to see her unless I’m absolutely sure she’s worth it.
She claimed the reason why she was looking for Men in Tampa was because she planned on relocating here once she finished her medical program. Fair enough.
When the Woman is More Masculine Than You:
When I spoke to Aleah, she had the voice of a beautiful woman, but her charm, tone, and the words she used were very masculine in nature.
No words of affection. She didn’t know how to flirt. It was very business oriented. When I’d get off the phone with Aleah, it felt like I just got off a business call with an HR representative, more than with a potential love interest.
She’d ask me direct questions about my future, finances, and career. And when I’d tell her, she’d didn’t compliment, praise, or ask follow ups to dig deeper. She’d just move on to other questions as if she was reading from a list on a clipboard.
It was a very weird and emasculating feeling because, I think a lot of us men were raised to think women were supposed to be the more affectionate gender. A lot of us were raised to think Women were soft, lovey-dovey, and romantic while we Men are tough, strong, and rugged.
So, if you come across as more sentimental than the woman you’re dealing with…it really is a disgusting feeling.
And I’ve seen women complain about the opposite when it comes to men. They’ll say that we’re too soft for wanting to talk about our feelings or wanting a woman to be their “momma.”
Even OTHER MEN will criticize guys for wanting to talk to their girlfriends about their thoughts, feelings and emotions…listen…maybe I’m just different. If that makes me less of a man or not as masculine…Sorry, but I refuse to get married only to continue to feel alone because I have to pretend to be someone else, just to be with someone. (seriously, do you hear how stupid that sounds?)
“But Rock! That’s what your male friends are for.”
Yes…because that’s what men are stereotypically known for. Wanting to hear the thoughts and feelings of other men. Not to mention, it’s rare to find a peer who actually likes to think beyond the surface.
“Well, maybe you shouldn’t be so sentimental. You should be like our fathers and grandfathers who kept their thoughts to themselves. Stoic and reserved.”
That’s not who I am. I can pretend and put on a performance for your respect and adoration but I’m not looking to get married to a guy, or women who think and act like men.
Also…IMO, a sign of true masculinity is having the strength to not give a **** about all these one-size-fits-all boxes and cliches about what masculinity is. That’s demonstrated by my resistance to the hook-up culture.
That’s right, fellas…FELLAs…for all you Andrew Tate/Kevin Samuel fans who want to look down on me for the sin of being open and sentimental with my women, at least I’m masculine enough to prioritize fatherhood and making an honest woman out of her.
So, when I say I’m different…maybe now you know what that means.
What spelled the end for me and Aleah was when she asked me how I felt about “Feminism.” At this point, I was genuinely afraid of losing her, but I spoke the truth as I knew it.
I told her, “Depending on who you’re talking to, you’ll get different definitions about what Feminism is. Some say it’s about equality. Some say it’s about special treatment.
“And once upon a time, I saw myself as a Male Feminist who believed in looking for my equal. Not someone to lead or follow, but someone to walk hand in hand with. But that’s when an Aunt told me that, as Christians, we’re taught that husbands are to be the head of the households. They’re to honor their wives but wives are supposed to submit to their husbands.”
Aleah’s answer to me was well-worded. She said:
“I believe people pick and choose what they want from the Bible. Society has now moved to a place where the household can rarely run off one income. And for centuries black woman have had to be the backbones of our families due to a myriad of systemic issues.
“So you can’t expect to be the man of the house, not support women’s equity, and expect total submission when you are requiring your woman to go to work and contribute things that are traditionally under the husband’s umbrella. That’s my issue. Having to work outside of the home and traditional wife chores. Meanwhile, what has been added to the husband’s responsibility?”
That’s what she said, verbatim. Surprisingly, I still had the text messages on my phone.
The thing is, I understand where Aleah was coming from. A lot of men claim they want to be in charge and when you ask them why, they’ll just say “tradition” or that’s how they were taught.
So, if they came up against Aleah’s logic, she’d likely win that argument because you can’t dispute what she’s saying.
The problem is, Aleah is thinking in terms of money, societal expectations, and her own personal understanding. The scriptures tell us not to do that. (Prov 3:5-6)
I don’t believe men should be the head of the family because of what humans say. I believe it because God says it. (Ephesians 5:22)
So, with respect, I responded with, “Well said. I’m not sure about those other dudes you’ve dealt with, and I definitely don’t care what society expects of me or my wife. All that matters is what we as individuals think. As long as we’re in accordance with God’s word the Bible, we can determine our own expectations and responsibilities.”
Our text messages started to fall away soon after that. Aleah’s not a bad person, but I could tell being with her was going to be a bit of work…all for a person who was well over seven hours away and didn’t know how to flirt.
That “bit of work” part cannot be overstated. Because the common retort is, “Are you afraid of a challenge?”
You mean…like the challenge of losing 178 pounds and keeping it off? Or the challenge of reading the entire Bible and committing my life to Christ in a world that’s getting more secular?
Or perhaps you’re talking about the challenge of writing and publishing my own books? Or the challenge of getting up at 5am twice a week just to go to boxing class? Or maybe the challenge of becoming the president of my department’s first Toastmasters?
No, ladies. I’m not afraid of a challenge. But you see my point? The journey of life is already full of challenges. Why on earth would I want to come home to a challenge when, guess what, I don’t have to!
Marriage will be difficult as it is when it comes to the challenges of raising our children, financial hits, and the pressures from other family members. When men say we’re looking for a woman to be our peace, don’t dismiss that.
Being with a woman who also strives to live by Christian principles…in my opinion, it does make life a bit easier because we can turn to God for answers. Thus, even if you are a more “masculine” woman who likes to lead and take control…if you submit to God’s scriptures, I do think you’ll naturally become more feminine because he does call you to be a helpmate to your husband.
If I may use my fiancee as an example again, she’s an HR manager and the 2nd eldest of 7 siblings. She’s a general the way she’s ordering her younger siblings around to get things done. But when it comes to me, she’s a bundle of clouds. Soft, attentive. She listens and follows my lead. Which, if she could type herself, she’d tell you that she actually appreciations and prefers that role. (of course, it also requires being a man who’s competent, intelligent, and responsible so she sees you as worthy of taking that husband role)
Patricia – The Girl Who Was “Too” Christian?
I don’t like to say that I “dodged a bullet” about girls I used to talk to, but Patricia really did have signs of mental instability…inconsistency with her logic and behavior was evidence of that.
In October 2021, Patricia was the first and only woman I matched with who finally lived here in the Tampa Bay area. She was in her early 30s. Light-skinned, mixed or Latino. Off the bat, Patricia had a bunch of red flags that may have been me being over-analytical.
I’m not a “simple” man. I don’t just listen to what a person says, but I’m aware of what they chose not to say. If you leave room for speculation, I will.
As I asked about Patricia’s background and living situation, she wouldn’t give me direct answers, but instead gave me clues. Very evasive. From the clues she gave, I was led to believe that she was living out of her car while renting her home out to someone else. Why was she doing this? God knows.
While her faith in Christ was strong. It was also a bit extreme.
For instance, let’s say there was a spectrum of how strictly a person lives by the Bible on a One to Ten.
Two is for the Lukewarm Christians who don’t see a problem with homosexuality or sex before marriage. Four is for the Christian Feminists who reject the Scriptures that talk about the roles of men and women.
I think I may be about an eight. Not perfect. I still have vices and inner demons that I’m wrestling with, but thankfully God’s given me the discipline not to act on my impulses.
Then you have someone like Patricia who’s not just a Ten, but I’d give her a Ten and off the rails. I’m talking about the zealous Christians who remind you of David Koresh from Waco who claimed to be God fearing, but also had sex with his parishioner’s wives with some misguided notion about saving the husbands from sexual sin (true story).
Similar to Aleah, Patricia didn’t exactly know how to flirt or demonstrate affection. She was hung up on the Bible’s warnings about lust. Which is kind of admirable, but also illogical with how far and inconsistent she took it.
For instance, She had already seen pictures of me from Match.com but wanted more selfies of me flexing (like the above pic). Then she got mad at me when I spoke to her romantically. You know, as if I wanted her to be my girlfriend.
For instance, one time when I texted “good morning” at 8:57 am, she waited until 1:47pm to say “Thanks you, too.”
That was the only text I got from her all day. I correctly assumed that for some reason, she was turned off by my words of affection. So, that night I changed up my style and said, “What up homie! How was your day?”
She literally responded with, “Haha! I was gonna say. It’s weird flirting. Like, I don’t know you so I feel like it’s fake. Sweet talk, it’s weird unless you’re already in a relationship.”
She’s responding as if I just met her that same day off the street. It’s been over a week and we’ve been sending texts and selfies all this time.
So, I replied with, “Yeah, sorry about that. It’s just my own style of flirting where, if I’m interested in you romantically, I start to text and show you affection…romantically. Otherwise, it feels like I’m talking to a buddy. Lol, and if I’m just chatting with a buddy, I should probably keep looking for a potential girlfriend.”
She said, “You can if you want.”
So, I said, “Is it okay if I go ahead cancel our planned date on Sunday too?”
She said, “It’s been canceled since you don’t respect my beliefs on flirting.”
That’s all a true story and it blew my mind. And forgive me if I was in the wrong when it comes to flirting, but from my interpretation of the Scriptures…I don’t think I read anything that implies it’s a sin. Trying to tempt others to do something sinful is wrong. But using your words to express romantic interest…I do wonder how she’s going to get by.
Either way, when I say all that was exhausting, it really was. All the anticipation, the hope, the stress, the deliberation on what to say and that throbbing in your chest when they respond…I was definitely fatigued with online dating after Patricia.
I’d eventually try e-harmony after that, but for issues I already mentioned in a previous post, nothing came of it.
After that, I left dating apps alone for the next three years until February 2024. My next Post will discuss my last failed matches from 2024, and how I eventually landed the one I’d marry.
Stage In The Sky 