The Date That Made Me Question All My Life Choices

I recently re-joined Match.com and started chatting with Sabrina. She was attractive, had a great job, and claimed to have an amazing sense of humor, so we made plans to get drinks. I walked in the door at 5:54 p.m.—a detail that will become important later.

When we met, she actually looked like her pictures, which was a refreshing change. But then something odd happened. I asked her about her Easter dinner, and she replied with three words: "It was fine." Okay, so I asked if she'd done anything fun with her family over the weekend. "Not really."

This went on for the next half hour. I’d ask an open-ended question and receive a one-to-five-word response, followed by silence. I didn't even get the unimaginative follow-up question, "What about you?" It seemed like even "You?" was too much to ask.

After about 20 minutes of this, she finally offered, "I don't have much to say sometimes." No kidding, Socrates. I asked her if she wanted another drink, and she literally just shrugged her shoulders, unable to utter a syllable. I took that as my cue, called for the check, paid it like a chump, and mercifully, the date ended.I got back to my car at 6:32 p.m.

The lesson: If you're on a terrible date with someone you know you'll never see again, and she offers to split the check, don't be a hero—just split the check.

How to Talk to Women: A Field Guide for the Socially Awkward

This post is a straightforward guide on how to approach and talk to women, based on personal experience. The author's perspective is built on two key realizations: getting older and "not giving a fuck." This shift in mindset changed a self-defeating thought process that once prevented any attempt at conversation.

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Key Takeaways & Actionable Advice

1. Practice, Practice, Practice

• The Goal: Not to get a date, but to simply start a conversation.

• The Method: Spend one day talking to five attractive women.

• Example: See a woman in a grocery store? Make a simple comment about a product, even if it's a "small white lie."

• Likely Outcome: 98% chance she smiles, says thanks, and moves on. The more you do it, the easier it gets.

2. The "Magic" Pickup Line

• Simple is Best: The most effective "pickup line" is "Hi" and a smile.

• What to Say Next: Have a relevant, non-offensive follow-up comment ready.

• Handling Rejection: If you get a blank stare or rude response, just smile, take a deep breath, and move on. You've dodged a bullet.

3. The Worst-Case Scenario

• The Experience: The author recounts a woman who told him she didn't date "bigger" guys.

• The Lesson: This type of cruel feedback is a reflection of her character, not your worth. Realize "what a bitch" she was and move on.

4. Give a Little "Shit"

• Be Playful: Be polite and nice, but don't be afraid to poke fun.

• Example: If she disagrees with you, jokingly say, "Thanks for screaming at me."

• Why it Works: This can put her on the defensive in a playful way, continuing the conversation. If she flips out, you just saved yourself from dating someone who's "uptight."

5. If She's Not Interested, Move On

• It's Not Personal: If you get a "no," or she blows you off, just move on.

• Perspective: You likely won't see this person again, so there’s no harm in trying. (Unless she's a co-worker or boss—in that case, tread lightly).

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Final Thought:

If you never try, you've already lost. The worst that can happen is you get some practice, maybe make a friend, and flatter someone. Life is short, so don't live with the regret of not saying "Hi."

Why "Perfect on Paper" Doesn't Work

My friend is a stand-up guy—a successful man who works hard for his family. On paper, he hit the jackpot with his wife: she's beautiful and comes from a wealthy family. It all makes perfect sense, like a financial statement written in cursive. Yet, watching him, it's clear that life isn't a spreadsheet.

I recently found myself in a similar boat. I met a woman who, on paper, was a slam dunk: low-drama, attractive, kind, and considerate. She had everything I thought I wanted, but for some reason, the chemistry just wasn't there. At 31, I felt the pressure to "buy in" and settle down, but no amount of mental gymnastics could make it work.

In the past, I’ve definitely been a victim of "good enough." I stayed in relationships that weren’t making me happy just because an attractive woman was interested. As a friend once wisely put it, "You start ignoring red flags, and one day you look down and you're standing on a huge pile."

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The Blame Game and the "Spark"

So, why do we stay in these situations? And why do we blame ourselves when a seemingly perfect relationship fails? I felt guilty that I didn't like my ex as much as she liked me. I've been ruined by the few times I've felt that unmistakable "spark"—that lightning-bolt moment when you meet someone and everything just clicks. Your heart races, you blush, and you start fantasizing about a future that includes this new person.

But when that spark is missing, we often fall back on old habits. We get lonely and question our own worth, thinking, "Why would anyone else love me?" We go back to bad relationships, conveniently forgetting the pain and romanticizing the good times. We choose the wrong people because we know they'll accept us, even if it means more pain down the road. We basically go back for seconds and ask, "Thank you, sir, may I have another?"

The bottom line is this: If the spark isn't there, don't cling to the hope that it will magically appear. You owe it to yourself to believe you're worthy of a relationship that ignites your fire and brings out the best in you. It can be a lonely road, but you deserve more than settling for "good enough." You deserve to be decent to yourself.

Review: OkCupid.com (I'm going to hell...)

Dating Site Debacles: A Look at OkCupid

Based on my site's traffic, it seems people only care when I write about other dating sites and porn. (On a side note, apparently, I’m a big deal in Turkey. So to Turkey, I say, “How ya doin’? Way to be Muslim without being jerks about holding women back. And democracy—not bad, right?”)

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My Review of OkCupid

This isn't my first time on this site. A few years ago, I used it and met a woman. By "met," I mean she said hi and immediately started sending me naked pictures. I’ll be honest, up until that point, I wasn't sure women like her actually existed. We eventually agreed to meet for coffee on a Sunday morning. Within an hour, we were headed back to my place for some sexual relations. And within an hour of that, she was on her way home. We never spoke again. Weird? For sure. Random? Absolutely. Cool? Kinda, but it’s definitely in my Top Five Weirdest Moments Ever (along with the time I accidentally touched SpongeBob SquarePants inappropriately and a night in Vegas that involved three different continents).

Since Match.com costs money and I'm currently unemployed (thanks for nothing, college degree), I decided to check out the free options. I’ll give OkCupid this: it's not PlentyOfFish.com (more on that in a later post). OkCupid has you set up a standard profile with a picture and asks you a series of questions. After you answer 25 of them, the site generates a compatibility percentage for you and gives you three matches, which they call The Quiver. As you answer more questions, the site reveals how compatible you are with each person, which is a pretty cool feature.

What the site also tells you are the chances that your match will reply to your message. In short, welcome back to middle school, motherfucker. You can read a profile, like someone, but then see that they are "VERY selective about who they respond to." Well, my confidence was sky-high until I read that nonsense. So, whether I like it or not, I have to factor that into my decision before messaging anyone.

And here’s where things get weird: I see a girl I went to high school with. That in itself isn’t very interesting—until I remember she's the girl my buddy, Mike, lost his virginity to. Suddenly, my mind, which has been battered by years of poor decisions and alcohol, remembers every damn detail of them having sex. She liked sex in public. She liked sex often. In short: she liked to hump. A lot. At 31 years old, I should be able to think about something other than that, right? Nope. I eventually decide not to message her because I heard Mike has warts on his ding-dong. Is it true? Were they from her? Does Mike like Asian hookers? I couldn't find the answers, so I decided to move on.

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Final Thoughts

The site seems okay, but I have no idea if it produces any results other than random coffee shop hookups.

You’re probably thinking, “Wow, this is a pretty shitty review... It seems like nothing more than an excuse to tell a story about some random sex you had and to talk about a girl from high school.”

Hi, have we met?