Four women in four cities take on 365 dates between them. Follow their adventures and misadventures.

57. Date Gone Downhill – Mr. Not Interested Would Disappoint Me

This is Rachel’s date 2 with Mr. Not Interested Would Disappoint Me. Read their date 1.

At some point in the dating process, most men will fall into the one of the following categories:

-Those who deserve your cold shoulder.

-Those who deserve your middle finger.

-Those who deserve your heart.

Maybe it is a hazard of my profession or a result of my desire to be loved, but I have always been quite generous with my get-out-of-jail-for-a-low-bail card when it comes to guys with both good looks and likeable personalities.

Things did not work out with Mr. Man Boy —who had more like 10 second chances—nor any of my 3six5dates.com bad boys, including Mr. Very Much My Type (Date 48), Mr. VIP (Date 40), and now Mr. Not Interested Would Disappoint Me.

First of all, I cannot believe I just went on a second date with a man who initially wanted to spend the date smoking weed at his apartment!

When I declined, he texted: “Contact me later if you are bored. I am just going to get stoned and play Rock Band.”

Since I have no problem calling men out on their bullshit, I texted back stating that I did not want to see him anymore because we had “lifestyle and personality differences.” He immediately picked up the phone to find out exactly what I meant.

“I don’t want to date a pot head. If you smoke weed every day, this is not going to work for me.”

But, Mr. Not Interested Would Disappoint Me knew the magic words. He told me that he honestly wanted to give up his pothead, party boy ways for a serious relationship, that he is depressed because all his friends are married with kids, and that dating is way more important to him than smoking weed.

Couple that with a series of compliments beginning with “I don’t meet women like you” as well as a dinner invitation to a hot restaurant, I had decided he had proven his worth.

Of course, he totally blew the date by trying way too hard to convince me to like him. He even asked me to dinner with him on New Year’s Eve.

But, I am grateful for this awful experience because it gave me insight into my own psyche. Two dates with him was all it took for us to play out what I now realize is a pattern for me.

It goes something like this:

Girl meets boy. Girl likes boy. Boy does something girl does not like. Girl confronts boy. Boy jumps through hoops to prove his worth to girl. (Or is sometimes just really cute and charming!) Girl gives boy a second chance. Boy blows second chance. Girl breaks up with boy.

And with some extra special men it continues on with a third blown chance.’

But I have been there, done that, and not doing that again.

Fortunately, between Mr. Not Interested Would Disappoint Me ’s desperation and my lack of desire to reform a noncommittal bad boy with a penchant for drugs/alcohol, I was able break my pattern.

But what if the next guy was a little less desperate or a little more charming?

Do you see the same patterns, men disappointing women and then winning them over again by chasing them? Do women place too much importance on men chasing them to prove their interest?

If a man is not willing to chase, is he worth it?


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