After a countless number of first dates (47), I had decided that I had to do something about my self-esteem before my self-deprecatory comedic nature led me to laugh with my friends about how much of a loser I am until my thin veil of happiness melted in a fit of unbridled rage against people that formerly would have identified me as a friend.

I needed an ego boost. I am not happy or proud of the way I tried to do so. I decided to accept a date with any woman. I arrived at the restaurant early because I was still nervous. As I sat there looking at the wait staff who had to have reluctantly agreed to all wear horrible Halloween costumes, I figured that nobody in this restaurant except for the old man drinking by himself was truly happy. The date was pleasant. We had good conversation and the food was equally pleasant. Though I was not attracted to her, and her voice reminded me of my step-sister, who I like, but I do not want to date, she was very nice. The day after the date, I received a text that I had previously sent out 47 other times. It said she had a great time and wanted to hang out again this weekend.

I knew exactly how she felt at that moment, and I know exactly how she would feel if I didn’t respond. It is one of the worst feelings I’ve ever experienced. It’s just complete rejection after pouring your heart out for an entire evening to a total stranger. You stand by your phone waiting for that buzz that never comes. You can’t eat or sleep, and getting up for work is even more of a chore. I had to send her something, but I did not want to go out with her again. Next week, I will tell you what I eventually said, and how she responded.

Halloween is fun: we get to dress up and pretend to be someone (or something) else — usually a sexier, sluttier version of whatever costume we choose. And playing pretend as if we’re back in grade school allows us to let loose and have a heckuva lot more fun than we usually have in our normal doldrum lives. It’s a win-win situation. Too bad there aren’t more opportunities to get out of our own heads. Whatever you dress up as tonight, take some great photos that show you having a ton of fun and add one to your 100hookup profile. It’s the perfect chance to capture your silly side for all to see!

I went out with a couple friends last night (Saturday) for almost Halloween night.  We went to a popular coffee shop, and tried to think of ways to talk to women we knew we would never go through with.  I was leaning towards the, “Nice costume, can I buy you a steak?” approach which was odd because not only is that weird, but also we were nowhere near a venue that had the capacity to serve my lovely lady a fine steak.  Instead, we sat there like morons comparing coffee patrons to celebrities.  We all decided that this one dude looked exactly like famed murderer and person-eater Jeffrey Dahmer.  He looked pretty creepy, and sat by himself.

A few minutes later all of the lights on the patio shut out.  About ten minutes after that, people started running out of the shop yelling that it was on fire.  My quick, reflexive instincts told me to stay where I was and watch.  The fire kept building until we were forced to leave.  We decided to go to a bar.  As a side note, the coffee shop was essentially ruined the next morning.

At the bar, many people were dressed up in elaborate costumes.  It was either almost Halloween or we were at a really progressive place.  I started a conversation with a zombie who I assume was female.  Though undead, she was able to convey her personality through a complex system of grunts and blood-spurting.  It took me a while before I started to think that she may actually be a zombie.  I maintained a conversation but kept a safe distance.  I offered to buy her a drink, but she kindly said “No, thanks.”  Really?  I even strike out with post-apocalyptic daemons.

I looove Halloween, what a great holiday! It’s a fun opportunity for us to act like kids without apologizing for it. Being a brunette who’s petite, yet curvy, a sexy Wonder Woman costume seemed to fit the bill. As I searched for Superman/Clark Kent (no doubt a great how-we-met story don’t ya think?) some other treats passed me in the early evening. What a fun time Halloween is.

It’s that time of year again. It is in the air, Halloween.  A few weeks ago, while visiting my parents, I asked each one of them what Halloween was like for them as children.  Their answers were completely different than what I had conjured up in my own mind about each of their childhoods.

My mother was raised as a Conservative Jew. Her father was very observant and did not believe in putting any time and/or energy into holidays that were not strictly hookup. My mother who grew up in New York City wasn’t allowed to trick-or-treat. She never dressed up, felt the excitement all day at school, or got to look forward to the chocolate bar before bed on Halloween night.

 My father was raised as a Reform Jew and was able to partake in trick-or treating. I always imagine his early years as Leave it to Beaver. He had an older brother, a working father, and a mother who seemed to be able to fix any problem in 22 minutes or less. His Halloween night was spent in costume going door to door collecting money for Unicef. Again, no chocolate bar before hitting the pillow for the night. But, what a concept; spending an evening with friends doing something for someone else. How many of us really, truly do that?

I grew up waiting for the one night of the year to collect as much candy as possible.  My brother and I would compete to see who could get more. It is not easy to admit, but at times I’m still like this. Putting my needs, even if they are just a hankering for a good old-fashioned chocolate bar before someone else’s.

If for just a few minutes a day we were to all do something kind for someone else I believe this world would be a much happier, kinder and gentler place. Think about this next time you go on a date.  Put yourself in the other person’s shoes for just a few moments. If you feel nervous imagine how the other person must feel. It takes a lot of effort to date and to put oneself out there. It makes us vulnerable which can be a scary place to be. Be kind with your dates. Honesty, integrity and helping someone feel more at ease are all signs of great character.  Make these attributes part of who you are and treat people in a manner that you would like to be treated. In essence, collect for Unicef on Halloween night, instead of going out there for as much candy as you can get your hands on. You still get the pleasure of trick-or-treating without gaining an ounce, and you did something good for someone else.  I imagine if we all took the time to do this all of our dates would have much happier endings.

My favorite holiday is right around the corner, the one where you get to dress up and masquerade around Hollyweird dressed as a completely different person. A free pass given to every girl dressed with skirts so short there’s no point to wearing them at all, and guys can gawk without being even remotely discreet about it. But aside from all the carnal couture and faux freaks that scatter throughout the city, the holiday entitles you to be whoever you want for one night of debauchery in lieu of another night of the normalcy we all know and abhor. So don your most shocking American Apparel and stalk the streets in something sinfully sweet, because the expiration date on this fantastic free-for-all ends promptly twenty-four hours after the start of All Hallow’s Eve. So find a trick, or a treat, or if you’re lucky – you’ll get to enjoy both.