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The 30 Day Online Dating Challenge!


Welcome to the 30 day online dating challenge…with a twist!

Dating someone online is like diving head first into a pool of Jello – seems like a fun new idea but when you actually jump in, it may not be everything you expected.

Meet Jeff. Jeff (name changed) is a single man with no children in a major city. He’s tired of the blind dates, meeting random women in the grocery store, and especially the hook-ups from friends. Jeff agreed to sign up for an online dating site and allow me to document his experiences for 30 days.

I asked Jeff about his expectations and he said, “It’s almost like you are trying to win the lottery. Maybe you don’t really expect to win, but you want to.“ But he was all in to give it a try!

There’s just one problem…Jeff had no clue how to write a profile.

I got a bright idea that adds a little twist to our experiment. I swooped in like Super Woman (but with a better outfit) and wrote Jeff’s online dating profile.

All the information is true. However, as a heterosexual woman, I have a pretty good idea of all the things that would catch my eye.

I vetoed the pictures he wanted to use that were bland or unflattering. Instead I selected more professional photos and some that showcased a little personality.

I picked out the best things about his personality and wrote them clearly, concisely, and with my own special brand of glitter. Basically I changed his original content of “I like hanging out, sports, and laughing with friends” to “I enjoy cheering (or booing) my favorite team and spending time with my friends cracking up. Life is way too short and I plan to enjoy it with great people and lots of jokes. ”

See the difference? Instead of just knowing the basics that sound like 1000 other profiles, we jazzed it up a bit and added a little humor too.

I also sent out Jeff’s first few messages to women. I showed him how to approach a woman online without sounding like a level 10 creep. Then I released him to the wolves to fend for himself.

Within 72 hours he had 10 messages and two dates lined up.

It’d be great if this was the part that I reported Jeff was out looking for wedding rings, but sadly the first two dates were HELL dates. But that’s the point of this experiment. We find Jeff a great woman and we learn something along the way about dating online and off.

Date #1
Scenario – meet at the mall and get coffee.

Did she look like her picture? Yes.
Did she seem surprised by you in anyway? No. She pointed out I looked the same.

How did it start? She brought a friend with her and didn’t tell me. I understand for safety but it was kind of awkward. They acted really goofy and it seemed fake. Almost immature.

When did it go to hell? We are walking and talking. Everything is OK so far. Then she says “What are we getting each other for Christmas.”

The look I gave her must have been deadly because her friend started laughing.

Then she says, “I don’t like surprises. I want an iPod.”

Gifts? An iPod at that? It’s only been 2 hours. The date was pretty much over after that.

The Lesson: Women, stop talking about commitment with men you just met. Gifts and expensive gifts especially, are the types of conversations you have with a REAL boyfriend. Not some guy who doesn’t even know your last name yet. She unknowingly gave off the impression of being a gold digger and possibly crazy (too much commitment too soon) with probably an innocent, absent minded comment.


Date #2
Scenario – meet at a local bar for drinks.

Did she look like her picture? Yes, but not as good. She was still cute.

Did she seem surprised by you in anyway? Yea, she thought I was a bit bigger (weight). Which I guess is a compliment right?

How did it start? I sat down and asked her if she ordered. I went and ordered drinks and an appetizer. She was friendly and smiled a lot.

When did it go to hell?
She started talking about her career and apparently she owns her own business.
I thought that was pretty cool. Then she asked me what I do and I stated I was in an entry level position with my company.

Before I could say anymore she cuts me off and says “So you’re just entry level?”

I said, “Excuse me?” and asked her what she said.

She went on saying, “Oh you’re just entry level, I have my own business, and blah blah.” She listed off her resume as if she was trying to show why she was qualified to judge me and say “oh you’re just in an entry level position.”

I told her that’s why she’s single. I paid for the meal and left.

If she’d let me finished I’d explain that I’m up for a promotion and have only been there since February. It’s a stepping stone for me to do what I want. I’ve run my own business but changed my mind about what I wanted to do this year and started over.

The Lesson: Before you shoot a man down because his job doesn’t sound like it’s up to par, ask him about his goals and maybe what else he’s done. When you jump to conclusions early in a conversation you may scare off a good potential mate. Get to know him and his goals before you judge his position in life right now.

I recommended Jeff try a little bit more patience as well. He was extremely offended but if he’d stayed to finish the conversation, he could have taught her a valuable lesson and may have made a genuine connection.

Our experiment is off to a rocky start but the messages continue to pour in to his inbox. Let’s keep our fingers crossed! Tune in next Monday for an update on Jeff’s 30 day experiment.

Are you interested in dating online? Do you need a little help writing your profile or a coach to get you started? E-mail me! [email protected] .

Dee Rene is creator of Laugh.Cry.Cuss. Visit http://laughcrycuss.com
and Follow her! Twitter.com/deerene_lcc


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