Cheeky Monkey Strikes Back

Just when I had given up, after not having heard from Cheeky Monkey in over 5 days, he sent me an email apologizing for having fallen off the face of the world and suggesting that we hang out soon. I am giddy like a school girl over the fact that I was wrong and maybe will see him again, but I am also skeptical. Is it really possible that he really didn’t time all week to drop me a little line? Seems doubtful.

Meanwhile, I have been spending a great deal of time with Spooner. We made dinner together last night and had some drinks and hung out watching teevee. And yet, despite how amazingly kind he is and how easy it is for me to be around him, still no spark.


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Guy #1: Cheeky Monkey

Cheeky Monkey


Cheeky Monkey is a graduate student of a certain esoteric field of study at a certain university in Los Angeles. He is near to my age, very intelligent, and fits my paradigm of what is attractive (namely, tall, lean, slightly aggressive, dark hair, almost stylish but not quite and clean). I met him via Craigslist, which is likely not a good way to meet quality people. But alas, I am both slightly desperate and resilient to facts, and so I will try this out just the same.

The History:

Cheeky Monkey and I have been on three dates thus far. The first was to a Mexican restaurant on the Westside of town. The food sucked, but the date was good. We stayed out chatting and such until the joint closed down. Date two was too a success, the both of us having enjoyed a nice meal at a wine bar/cafe followed up by some fun time at my place. Third date took place at his place and resulted in an overnight.

The Good:

Cheeky Monkey and I have a great deal in common, but not so much that it is creepy. Conversation always flows nicely, there are things we both want to do and places we want to go – possibly together. Making out with him is a great deal of fun. He has good manners and hygiene and best of all, he is super duper smart. And did I mention he is cute?

The Bad:

Cheeky Monkey is a broke broke student. He also has two very silly tattoos. Relics of his youthful idiocy, no doubt – but permanent just the same. Also, I get the sense from one off comments that Cheeky does not have any sort of real connection with his family (I do). And finally, he may be selfish. And so am I. And selfish girl plus selfish boy makes for bad relationship.

The Confusing:

I am pretty sure he is not interested anymore. Although he being a confusing male and me being a failure at realizing/acknowledging dating signals, I can’t be sure. But basically, last time we went out, I ended up spending the night at his house. Good times were had. The next morning, we went to breakfast, after which we parted ways. About two hours after I left, he sent me a text telling me what a lovely time he had and asking how my day was. The following day, I asked him if he wanted to partake in a certain activity with me. He told me his weekend was booked because of some horse dung reason, and that we should do my suggested activity the following weekend instead. I have not heard from him since. What I don’t get is what happened between the text where he had a great time and now?

Update: No word from Cheeky Monkey for three days, although we technically have a date scheduled for next weekend.

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And so it begins.

With a mouth full of sass, a heart filled with hope and a brain full of skepticism, I embark on my dating Odyssey. This self proclaimed Eastside Hipster (though I barely live on the Eastside and am most definitely not hip) is going to date like there is no tomorrow – or more likely until she gets tired of dating. And not only that, but she is going to document it. Because dating is confusing and tiring and funny and amusing. And this Datester sucks at it and needs your help. So please, as you read, comment, email, yell, fall in love with me, whatever – just help me decipher this crazy work of LA dating.

Should any person I mention on here come to find this site, and should they have enough self-awareness to know that I am speaking of them (so few people do), I apologize to you for any unkind words I may have said. In fact, I am sure that you are perfect, wonderful and a whole host of other really super adjectives – and I am wrong. So yeah, don’t be sore about it, mmm k?

Onwards we go.

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