The Inadvertent Misogynist, Confessions of a Serial Dater

Serial Dater [cereal-daytur]

-Noun.

*A man or woman who non-exclusively dates multiple partners at times in an unscrupulous manner.

Synonyms: Whore, Player

Antonyms: Prude, Nun, Dungeons and Dragons Aficionado, Mom

I’m a thirty-something guy living in Boston.  I developed an interest in serial dating 2 ½ years ago and it subsequently has been a hobby of mine ever since.  I knew with my penchant for dishonesty and strong desire to hone my time management skills that I had what it takes to be a womanizing dickhead.

I decided to almost exclusively meet girls online.  Why you ask?  Because they put out; quickly.  Even though that’s true, I more so wanted to leverage my time by placing ads and focusing on courting women who already had an interest in me.

So I created a number of different ads, from brutal honesty to complete nonsense.  To my surprise, nonsense was by far the most successful.  I eventually created an ad that received countless praise.  Over time I heard from hundreds of quality girls from ads I placed on a dozen different websites.

Before meeting I preferred to converse by email, IM, or texting.  This way I was able to put more thought into what I had to say and flirt with the utmost precision.  Better yet, I could be an uber-prick and pretend to speak multiple languages compliments of Yahoo! Answers or AltaVista Babelfish.

When starting from scratch I usually had eight to ten viable prospects, from which I would pick five to six to meet, and then cut it down to my favorite two to three.  It was important to meet as soon as possible to avoid days or weeks of communication only to discover you aren’t the least bit compatible once you finally meet.  Sometimes I’d be invited over to their house at 1:00 am because they just got in from a girls night out and couldn’t wait any longer.  I called that “a guaranteed lay”.

I know ways to succeed when dating two or more; however, in my opinion, dating more than three is virtually unmanageable.  You’ll have no time for your friends, the gym and be tired every day at work.  Therefore juggling multiple relationships requires some strategy.

1. Determine desired level of honesty: From my experience if you want to date and sleep with whomever you want without the risk of losing what you have, lying is pretty much required. For example, at one point I was dating 5 girls at the same time and sleeping with 4 of them.

Moreover, I probably would have been smothered in my sleep if they knew I lined up meetings with girls I was dating at strategic times of the day.  I’d have a nooner with one, an at home dinner and movie with another, and a late night sleep over with a third all in the same day.  Don’t worry ladies; I’d wash up in between… usually.

2. Positioning: Assign each girl a rating of ‘weekday’, ‘weekend’, ‘casual’, and ‘I got nothing else better to do’.  Fridays and Saturdays are reserved for the girls that you may actually see a future with or are serious arm candy.  Conversely, that one who’s been reading “he’s just not that into you” will still be there when desperation sets in no matter what she says.

3. Preemptive damage control: Be proactive and learn techniques on how to block the dubiousness.  For example, if asked where you were the night before, you need a way to say it softly or construct a canned lie that works best for you.  I liked to say “I was with my friend ‘so and so’ and we watched a movie” instead of, “I hung out with Jennifer who I’ve been fucking the entire time I’ve been with you.  We went to a movie and she blew me in the parking lot afterwards.  So how was board game night with the family?”

So what came out of this debauchery?  A lot more than I bargained for.  Whether we are willing to admit it or not, we all want someone special.  This is a way to get to them quicker than ever; however, if you screw up, be prepared for a multitude of problems.

Four girls were in love with me at the same time, I had to create an Excel spreadsheet just so I knew who to notify if the doctor gave me some bad news, two girls wet my bed, and worst of all I pissed off a few girls so badly they put up ads telling others to avoid dating me and to this day I receive harassing anonymous emails whenever I put up an ad on Craigslist.

So when asked “TSA, if you could do it all again would you change a thing?” I vehemently reply “oh fuck yeah.”

Well, loyal readers…please welcome our guest writer The Striped Avenger! TSA is in his early thirties, a lifelong resident of Boston and that’s all he’s willing to tell us.  He does, however have a lot to say about his stint in Serial Dating…so please leave him your comments below.  He’ll be happy to share the pros, cons and unwarranted high fives with anyone who cares to offer up their opinions!

Caution, Relationship Ahead

“The dread of loneliness is greater than the fear of bondage…”

~ Cyril Connolly

Romantic relationships are never easy. Even the strongest of couples hit bumps in the road from time to time. But when two people get into a commitment for the wrong reasons they are most likely headed for a major mishap.

“Accidental” relationships happen to people everywhere, everyday, regardless of sex. What do I mean by “accidental?” Quite simply, these individuals become submerged in a commitment that one or both never intended on getting into in the first place…all because instead of holding out for Mr. /Ms. Right, they have ended up settling for Mr. /Ms. Right Now. Sound familiar? Let’s all explore some different scenarios that can lead to accidental relationships with an imaginary couple, Dick and Jane.

The White-Knight Relationship.

In this relationship one party trades what they need (such as financial support) for what the other party wants; a commitment.

In this scenario our Jane is in serious trouble. She cannot pay any of her utility bills and is about to lose power. (Pun intended? Perhaps…) Jane tells her co-worker and good friend Dick all about her financial woes. Dick really likes Jane, (and he sees this as an opportunity to show her he could be more than just a friend), so Dick offers to pay her bill for her; and insists she can pay him back when she gets on her feet. Later that afternoon when they are leaving work Dick asks Jane out to dinner. Jane accepts. “It’s a date!” Dick says. A date wasn’t what Jane was thinking, but no harm in that, right? Jane goes on said date, drinks more that her share of the wine Dick purchases and when Dick kisses her goodnight that evening she kisses him back. The next night Dick offers dinner again, and Jane accepts again. Dick is so nice and so generous; and okay, it’s true that she isn’t attracted to him, but that can grow, right? A month goes by, and now Dick is introducing Jane as his girlfriend, she is about to meet the parents and he is talking about taking it to the next “level”. Jane can no longer deny it; she has slipped into the girlfriend role. Accidental relationship type number one: savior becomes suitor. Escaping would mean breaking her good friend and rescuers heart; (and she really can’t pay him back right now anyway). Easier to let this relationship happen, perhaps he will love enough for the both of them.

The Date-Night Relationship.

This is a relationship of pure convenience on one side, and (sadly) true romantic feelings on the other.

In this setting, Dick is seeing a couple girls, but nothing serious. Girls that he calls when he wants to see the new romantic comedy that he wouldn’t dare tell his guy friends he wants to see or if he needs a plus one for his cousin’s wedding. He calls on Jane for these occasions more and more; they have similar tastes in movies, and she really gets along with his family and friends, and of course the sex is good too. Jane is a great female friend…plus. But Jane is starting to be increasingly affectionate. She is calling him quite often between dates. Then one night she comes over and offers to cook instead of ordering the usual take-out. She’s brought a movie; it’s (uh oh) a romantic one. She snuggles up to him on the couch, where they end up falling asleep. In the morning Dick opens his eyes to see Jane staring at him with a strange smile upon her face. “I love you,” Jane murmurs. “I love you too,” Dick mumbles back without thinking. Voila! Dick has trapped himself in accidental relationship number two. He begrudgingly accepts this unintended commitment rather than dealing with the mess of breaking Jane’s heart. What started out as a pseudo relationship has become a real one. Dick will put off breaking Jane’s heart…for now.

The Bad-Habit Relationship (AKA The Crutch).

The fear of being alone is strong in some people. They learn to use others to insulate themselves…from the one person they least want to face, themselves.

In this situation, Jane and Dick meet at the book store. Jane has just ended a relationship and isn’t quite over it yet and Dick isn’t in a relationship because he just doesn’t really have time for (or want to make time for) one. They both know that neither of them is in the proper place in their lives for a commitment to another person. Yet they find themselves very attracted to each other in an oddly comfortable, broken in sneaker kind of way. Very quickly they start to spend all their spare time together. It’s never very exciting or romantic. Most of the time Dick is ignoring Jane while he works or studies while Jane sits on the couch watching TV and talking about her ex-boyfriend. They aren’t in a relationship because they like each other, they just like the idea of another person in the room to hear them breathing. This is ugliest of accidental relationships, and it can be the most dangerous because you are bonded together by mutual fear. Dick and Jane stay in the unhealthy bad-habit relationships for a long period of time, unhappy and miserable but afraid to make a change.

Relationships are supposed to be about love and trust and mutual caring. They are not supposed to be about convenience or fear of being alone in a movie theater, or worse, in your own home. These accidental relationships are not just a waste of your time but they can be damaging, especially if the other party is not aware that you are in it for the wrong reasons or worse, they are under the impression you are as invested in the relationship as they are.

We are not here indefinitely. Staying with Mr. or Ms. Right Now will in fact keep you from meeting people that might actually be a better fit. So if you find yourself in an accidental relationship, be it the “white-knight,” the “date-night” the “bad-habit;” (or any other in a long list of dire intimate dealings) do yourself and your contingency partner a favor and get off at the next exit.

Otherwise you might just crash into something a lot more dangerous, like an accidental baby… with that accidental partner…which could become an accidental marriage… and, well, you get my point.

For those of you that were looking forward to love-fucked part three, our most sincere apologies…my writing partner’s computer died on him and he is still in the process of rectifying the situation. So I hope you enjoyed this oldie but goodie from me…

Now! Weigh in! Have you ever gotten yourself into an accidental relationship? How did it happen? How did you get out of it? Or did you??