Matchmaking 101: Bachelor #2

To better understand the Match.com project, it should probably be noted that I have never actually been on a "real" first date.  To be honest, I have a tendency to fall in love with my friends, boys that I've had in my life for years who have slowly become irresistible to me.  This type of situation often lends itself to an incredible build up to the start of a relationship, complete with years of missed opportunities and underlying attraction, but it doesn't often lend itself to dating in the traditional sense.  Perhaps this is one of the reasons I have slight anxiety over the idea of dating someone brand spanking new.

Bachelor #2 was really my premiere first date experience for this project.  Yes, there were drinks with Bachelor #1, but the general feel of the meeting was more that of an interview than an actual date.  Bachelor #2 went a more traditional route: drinks and a show.

For an actress, I have been woefully neglectful when it comes to taking advantage of the Chicago theatre scene.  Therefore, when Bachelor #2 suggested we meet up to see the longest running show in Chicago, I was more than happy to agree.  The great thing about a show date is that it can be a bit of a first date cop-out: if there's no dinner or drinks beforehand, the pressure to interact with one another is limited only to the hour or less between meeting up in line and the show's start.  At first, I was more than willing to use this situation to my advantage and avoid as much awkward chit chat as possible. However, my financial backer and Miss X would have none of my avoidance tactics.  If the point of this project was to meet new people, I would have to carry on an actual in-person conversation with every date.  So I agreed to meet Bachelor #2 for drinks beforehand.

Much like the date with Bachelor #1, there was little difficulty in making conversation with Bachelor #2.  Ironically, having plenty to talk about seems to be one of the benefits of dating strangers.  Questions about family, work, and educational background are all on the agenda, leaving no shortage of conversational material.  I may now know more about Bachelor #2's childhood than that of some of my college friends. After all, I've never thought to ask someone I've known for years how many siblings they have or what their parents are like, but these are perfectly appropriate questions to ask during a date with a stranger.  Bachelor #2 and I even got around to discussing the traditional conversational taboos: politics and religion.  Why? Because we had nothing to lose in doing so.  Had we become repulsed by each other's viewpoints, we could have simply parted ways.  That's another benefit of the date with a stranger: there's very little investment at risk; should things turn sour with disagreement, just walk away.  Thankfully, there was no such conflict that night.

The final verdict on Bachelor #2:  Easy conversation and mutual interests made for a very entertaining evening.
We have tentative plans to see another show mid-week
...take from that what you will.

Matchmaking 101: Bachelor #1

Shortly after my profile went live on Match.com this past week, Miss X called to inform me that one of the boys she had 'winked' at had messaged me: "Message him back, he's cute and he does yoga."

As I checked out his profile later that day, I found that he was in fact cute and he did in fact do yoga, but what really sold me was that I laughed out loud at his email. [Funny boys are sexy.] So I replied.

Three or four emails later, we arranged for a weekend meet up to explore his neighborhood...that was today.

As fate would have it, it was a dreadful day to explore any neighborhood, with the kind of rain that spits down from the sky sideways and drenches your face even with the protection of an umbrella. To make the best of it, we decided to get a hot drink somewhere and try to wait out the drizzle. Unfortunately, the only cafe on the block was closed for a private party, so we settled for a beer at one of the bustling pubs.

How did the date go?

There wasn't a lull in conversation once, we laughed, we talked, we shared life stories...and neither one of us was interested.

But perhaps I've found a new yoga buddy.

Matchmaking 101: The Profile

Miss X should really work in sales. 

Here's the pitch she wrote for me: 

[and it seems to be winning people over]

...that pretty much sums me up.
She knows me well.

Matchmaking 101: What have I gotten myself into?

Yesterday, I came to the realization that I will pretty much do anything if it'll make for a good blog.

Let me explain: During a conversation about the current state of my love life with the most spontaneous boy I know, he suggested that I try to meet guys on Match.com.  I laughed and told him I'm not that desperate.  He then said it might make for a good blog.  That's when I gave it a second thought.  By the time he offered to pay the monthly fee, I was sold.

However, this project has a few rules:

1. I don't want to manage the profile.  This may sound weird for a blogger, but I'm kind of sick of describing myself.  Between twitter, facebook, myspace, personal websites, and various other online outlets, I'm sick of trying to define 'who I am.' Thankfully, my best girl friend [call her Miss X] was more than willing to take the job.  She created a fun and flirty description of me that was pretty much spot on.  Except I'm much cooler through her eyes.

2. I don't want to spend hours online sorting thru the profiles of prospective dates.  Truth time: I've actually done Match.com's free trial before [boredom will make you do crazy things...so will a bottle of wine & an evening of watching too many romantic comedies].  I hate having to sort thru thumbnail after thumbnail of guys trying to look cooler/thinner/hipper than they really are.  And reading email after email of "you fine, girl." isn't my cup of tea either.  That's why Miss X is my official screening process for this project.  She 'winks' at the goods ones and if they respond with an intelligent email, that's when I take over.

3. I have to go out on at least 4 real life dates in 3 months time.  My financial backer created this rule to make sure his money's well spent.  Originally our deal was one month of membership for 2 dates, but since he was feeling generous and paid for 3 months, the date number was increased to 4.  It should be noted that I haven't been on 4 dates in the past 2 years, let along in 3 months.  This could get interesting.

Let the games begin.