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The 30 Day Online Dating Challenge (Part 2): The Crazy And The Delusional


On our last entry, Jeff had just entered the world of online dating and experienced not one, but TWO hell dates.

Here’s the story in case you missed it: The 30 Day Online Dating Challenge.

Jeff decided to try something new. Several online dating sites now have “mixers.”
The purpose of mixers is to get everyone online to meet offline in a low pressure
environment. It’s like taking your friends/followers list and having a cocktail party.

One name tag and a few conversations later, Jeff is waiting in the “holding room”
waiting for the women to be let into the room. He described the situation as cattle. Men were herded into one room and women were then shuffled in after browsing the list of attendees.

Oh because that’s not awkward at all.

What did the women say when they met you?
Several of them complimented that I was attractive and had a good personality. I had a lot of women come up and talk to me. I was a little more dressed up than the other guys. They had on tshirts and jeans.

Did you meet anyone?
Yes. I connected with Jennifer who I found out works at my job. I knew she looked familiar. And a girl named Sasha.

Now here is where our story gets interesting….

Date #1: Jennifer and Jeff
The same night, Jennifer suggests that Jeff leaves with her to go watch a movie. She’s known him a full 25 minutes.

Jeff and Jennifer go to the movies and out to eat afterwards. Everything is good but Jeff is particularly cautious because she works at his job.

A few days later, Jeff and Jennifer are hanging out again and Jennifer reveals she has a three month rule.

How did that make you feel?
If I wasn’t a good guy, I’d just wait the three months, hit and then leave. When women tell you that it’s like a challenge. And she said oral was okay just not penetration so it’s confusing.

The Lesson: The 90 day rule is bullshit. It’s fine to have a vetting period to make sure someone is who they say they are and their intentions are clear. However, some (most) men view your grand announcement of a 90 day rule as a challenge not a boundary.

And what level do you have to be at the end of those 90 days? Do you have to be in a relationship? Or did he just have to hang out long enough and not get on your nerves?

Jennifer hasn’t shown him that her body is something precious. She’s shown him that her body has a timer (like an oven) and if he’s patient enough he’ll get the cookies. She didn’t identify any other factors that would open up her cookie jar other than time. She also invalidated her sexual activity rule by creating the loop hole for oral pleasure. Now Jeff is wondering if she’s just doing this for show or because it actually means something to her?

Some women have past issues that make them uncomfortable with full-sex so
they need oral first and then ease into the full-sex. Maybe the 90 days just had a good ring to it.

Has Jennifer had an experience that makes her uncomfortable? Or does she think holding out for the 90 days this will make him commit?

I wrote a detailed post on this already so I’ll just say that the 90 day rule isn’t necessarily showing or proving what you want it to prove or show. Jeff likes Jennifer but her 90 day rule, without proper explanation and detail, makes him a little cautious about WHY she REALLY has this rule.

90 day rule post: The 90 Day Rule.

Date #2: Sasha and Jeff

Sasha has one child and spent the entire first few minutes she met Jeff talking about how he’d be a great dad and how her biological clock was ticking…loudly.

Although Jeff left with Jennifer that night, Sasha called around midnight asking was Jeff free and if he was hungry.

Because of course all good first date dinner dates take place at midnight, right?

Jeff obliged and met her at a late night food place. They eventually ended up back at his apartment and well….

So what happened? I didn’t want to have sex with her because she kept talking about wanting a bigger family and I was afraid she was fertile. But I ended up satisfied still…and she didn’t let any go to waste. (she gave him oral sex)

Wait! But you just met her?
Yea so. Apparently she felt really comfortable because she’s read my profile.

Did you see her again?
Yes. Because she showed up at my job. The next day I’m outside on break and I see her walking up with a cookie tray. She made me cookies and showed up at my job to bring them to me. I never actually told her where I work. She played detective on my Facebook.

So how did that go?
I snapped on her. I was so confused and scared as to how she got there and why. She apologized and left. She continued to apologize via text but I wasn’t trying to hear it.

The Lesson: Apparently women feel a new level of comfort with a man they’ve engaged with online (or can read about online) than they do with strangers. The sexual activity on the first night isn’t the problem, the problem is Sasha crossed the threshold into crazy and or desperate.

Of course Sasha explained to Jeff that she really just wanted to do something nice
for him. I admonished Jeff for being so harsh with her because Sasha sounded sweet. However, ladies we must be careful about giving too much too soon. Your effort to be nice shouldn’t ever make a man question your sanity. Showing up at jobs is forbidden until you have something solid. Sasha is also really laying it on thick. She might as well put a sign on her head that says “I will marry you tomorrow!” You don’t need to be a rubix cube challenge to get a man, but he should have to TRY to be with you.

Sadly, most women can’t find the line between being overly available and impossible. Sasha was overly available and it backfired. It’s okay to save certain things for just boyfriends. Any man you are dating shouldn’t get everything right from day 1. Especially if he hasn’t yet shown that he wants that from you or that he wants to give his all to you too.

It’s getting really interesting with Jeff. Let’s see how this goes! Are you
interested in online dating or getting a coach to get you started? E-mail Dee at
[email protected].

Have you ever thought about online dating while IN a relationship? Catch MYA! Dee’s other woman in the experiment Online Dating While In A Relationship.

Dee Rene is the author of Laugh.Cry.Cuss
Follow the blog! @laughcrycuss
Or follow Dee @deerene_lcc


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  • Kia

    rule games and lies we play to meet mr right!! great article

  • sassy24

    0.o at these women

  • Yes! Desperate much?! Lol.