When It Comes to Dating, How Crazy is Too Crazy?

Dating is strange because we expose ourselves to so many fish in the sea. Some are crazy.

man in suit with woman behind him nuzzling his neck
(Image credit: Valentin Casarsa/iStock)

Dating is strange because we expose ourselves to so many fish in the sea. So, we meet many crazies in the process.

My friend (Jane) just dealt with the craziest guy I've heard of. His assortment of lies, tactics, and weird signals are Twilight Zone-worthy.

Jane met this guy (Mark) at a concert. She had attended Boston college, and this guy was from Boston and thinking about moving to NYC-a nice combination for Jane.

Her first impression was that he was a bit "douche-y."His family basically struck oil (why couldn't my family strike oil?) long, long ago and he gets checks every two weeks from Texaco. Thus, she saw him throw money around carelessly.

Jane and Mark hung out one night, kissed, and struck up a fledgling relationship. But this guy rivaled the protagonist of Poe's "The Telltale Heart," in his descent into madness (...very dreadfully nervous I had been and am; but will you say I am mad?").

Here are Marks' strange actions:

Excessive Texting Early On

Seems many guys are guilty of this behavior, and Mark was no different. After their meeting he texted every hour on the hour. In fact, he sent one text that was "Sorry if I don't text you for an hour it's because I'm in a fantasy football draft."

Jane was a little uncomfortable, with all this attention so early. When she confronted him about his "neediness" he said: "I'm not needy, I'm romantic."

Random Weird Video

Soon after meeting, Mark sent Jane videos of him playing golf. She was confused about why she should care. Random...and weird.

Unromantic Date Premises

Even though Mark said he was "romantic," he had strange ways of showing it. For a date, he contacted her and said: "I just won a huge bet, let's go out with the money and celebrate."

He followed this up with a three paragraph email explaining how he doesn't have a gambling problem, and he's not a bad guy.

Somehow I think going out together with gambling earnings is not romantic...neither are golf videos, but perhaps she was still buying his "romantic" description at this point.

I Miss You

After dropping her off at her apartment after their second date-the two spent all day together-- he followed up with a call saying: "I miss you." After two dates? Jane said it was "gross."

Creepy Text

After they spent their second night together (no sex), he texted her saying: "I'm so proud of us for not having sex."

A Secret Life on Facebook

As is often the case,Facebook truly lowered the boom on the relationship. You really have to wonder why this guy didn't audit his Facebook profile before adding Jane.

First of all, there was a girlfriend...or something that emulated a girlfriend. Here is a conversation Jane saw on Mark's Facebook from the night Jane met him (they hadn't spent the night together that first night):

Facebook Girlfriend: "Sorry I woke you up last night."

Him: "That's Ok, at least you had underwear on."

Jane mined other hidden gems from Mark's Facebook profile. It turns out all his trips he took with his "family and friends" that he told Jane about were actually trips he took with the girlfriend.

The kicker: Mark had sent Jane pictures of his "beautiful recent vacation in Nantucket." But these pictures were recycled from an older album, from a trip with his girlfriend.

When Jane confronted him, he told her that he's been through a year of mental trauma,seeing a therapist, and this is why he lied to her the whole time. She couldn't quite see the logic in that (much like most of his actions).

But the strange thing is that Jane, while no longer attracted to him, felt it was her duty to "be there for him," against her sister's and my objections. But eventually, Jane listened to us, luckily.

Why can't I meet a "too nice" girl. I text a girl one time: "hey want to get together," and I get ignored. Then I see stories like this.

Should I be more persistent, or act more outrageous?How bad am I if he can get dates with this behavior and I can't get called back when I act as normal as possible? Are most girls this tolerant - or do we wonder why Jane kept seeing Mark?

When would you get out of this situation? Personally, I would have been out of there after the texting, or definitely the golf videos (even pro golf on TV is boring). What's the most bizarre thing a guy has ever done to you in dating, or told you to excuse his bad behavior? What's your take on this situation?

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