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The 30 Day Online Dating Challenge: The Final Experiment


Thirty days are up and we must get the scoop on the last few days of Jeff’s online dating experiment. We’ll hear from Jeff about his overall experience and get an update on some of his more infamous dates!

Catch up if you missed it!
Part 1: The 30 Day Online Dating Challenge

Part 2: The 30 Day Online Dating Challenge: The Crazy & The Delusional

What do you think about the experiment overall?
It was good. I got out to see a lot of women and went on a lot of dates. Which was kind of expensive. Met new people and it was a new experience. And hopefully this last one can be my girlfriend.

If you had to do it all over again, what would you do differently?

I wouldn’t change much except I wouldn’t use the free site. The paid site was better. If you are paying you get more out of it and more people you’d be interested in talking to versus the free site.

Maybe I would sign up at a different time. I got more hits at the very beginning of January. Maybe people signed up to try something new with the New Year but my account has had a lot of hits in the past 2 days.

So let’s go through the dates that stuck out the most in your mind.

What happened to Jennifer also known as “Ms. 90 day rule”?
We did have sex after like 2 weeks. I wanted to see if could break the 90 day rule and I did. Which sounds horrible I know. It wasn’t like I broke it to see if I could, she wanted me to break it.

She told you that?
Yea. Jennifer said she knew she wanted to sleep with me when she first met me. When I asked her about the 90 day thing she said if someone sticks around that long then they deserve it. And she was seeing if I would stick around that long. But then Jennifer said she felt genuine about me and that something could happen with us so she gave it up.

Do you like her now?
Well no but not because we had sex so soon. I don’t like her as more than friend because…
If she made you wait the full 90 days and you were not interested in someone else,would you like her any more than you do now?

No, I don’t care about the 90 days. Because it doesn’t make any sense. You could sleep with somebody the first night and fall in love. Or you could wait 90 days and not feel anything. It’s about the connection not how long she made me wait.


I hear you had an interracial experience too! Tell me about that.

She treated me like a trophy. Like it was a prize she had black guy. She kept making comments like “I only dated three black guys, we had a good time and the sex was good. So I wanted to try it again.” Megan kept talking about how she likes hip hop music and black music.

So that was the end of that. She wanted a black boyfriend, not just a boyfriend.

Ms. “I own my own business” came back around. What happened?

She sent me a text and said that she wanted to apologize. She said she realized she was rude and could appreciate my honesty.

I told her about my promotion and the businesses I’ve owned in the past. Not to rub it in her face (well, kinda) but just to prove my point that she can’t judge people so quickly. She wanted to go out again but I’m good on that.


What about Cookie and Ms. I want an iPod?

I never talked to Cookie again and Ms. “I want an iPod” got cut off as well.


So tell me about the new girl Tanya.

She has an education, works hard, no kids and never been married. We started talking slowly on the web site then moved to texting. So it took longer with Tanya to move from the web site chatting to actually exchanging numbers.

Have you met her yet?
No she’s been out of town for the holidays.

You are already telling other people that you are “talking to somebody” so it sounds like it may be more serious.

It’s scary because I haven’t met her yet but she’s very genuine and we have a great connection. We are both in the same place in life and have similar romantic experiences in the past. We have a lot in common.

We talk or text every day. She has similar career goals as well.

Why are you cutting off other people prior to meeting her?
Because I think this has a lot of potential and I want to give it my 100%. And since it’s still early with the other girls it’s easier to cut them off now and focus on Tanya.

How does she feel about you?
She said she can’t wait to go on our first date. Says she feels the same way about me that I feel about her. We took our time and it wasn’t a rush.


Overall, what did you learn from this experience?

You have to get out there and try it. The love thing is a long journey but you have to try. You will probably meet some crazies but keep going. Be patient. It was worth it even though I spent a lot more money going on dates. I did meet at least one quality person and had a good time.


Jeff’s story makes me smile! He plans to keep his account open unless things become serious with Tanya. Although I did chastise him for some of his more hoe-ish ways during the experiment, I am glad to see that in the end he did find someone that has sparked his interest. We learned a lot during this experiment about how men approach dating and most of all how women can fumble some dates as well.

I want to thank Jeff for his participation and wish him all the best.

Do you need help with your online dating profile? E-mail Dee!

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