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: Online Dating Advice from Bachelor #1

One of the best things about meeting people from the online dating world is the fact that, while everyone's in the same boat, there are still varying levels of experience to be found in the situation.  On my date with Bachelor #1, I found that, though we had both signed up around the same time last week, this was not his first foray into online dating.  Apparently, he'd tried it years earlier and had some veteran wisdom to pass on to my rookie ways:

1. Assume that every date you meet has at least six other dates lined up after you.  Since I'm only just starting to dip my toe into the online dating pool, Bachelor #1 was my only prospect for this past weekend.  He, on the other hand, had three different dates lined up, two of which had occurred on the same day.  Some people might have found this fact rather insulting, I found it refreshing and smart.  You can't put much stock in anyone until you meet them face to face. Increasing your numbers puts the odds of meeting someone worthy more in your favor.

2. If both parties are willing, meet in person as soon as possible.  Similar to the multi-date rule, this one goes back to the fact that you can never tell how a meeting will go once you're in person.  Bachelor #1 told me a story in which he'd interacted with a girl online for quite some time, getting along famously, but when they finally met after weeks of typing, there simply was no spark.  Don't waste your time building a relationship with someone online unless you know that chemistry has begun to translate into real life as well.

3. Always be honest and up front about your feelings for the person you are meeting.  I could tell within the first few moments of meeting Bachelor #1 that, while I'd love to have him as a friend, I simply wasn't interested in dating him.  The situation was missing that undefinable quality that draws two people together; call it a spark, call it chemistry, whatever, it just wasn't there. Thankfully, we were both on the same page. Even better, we were both up front and honest about the situation.  There's no point in wasting a near-strangers time by trying to be polite. If you're not interested, just say so...your confession may even come as a relief.

Matchmaking 101: Dating Advice from a Boy

Tomorrow, I have a 'date' with Bachelor #1 of the Matchmaking Project, but more on him later...

Tonight, I bring you 3 fabulous first date pointers [for me or anyone], courtesy of my friend Los:

1. Be yourself.  You have a great personality when you show it off.  So show it off. 

2. He's not going to ask you to marry him...so don't be nervous. Come up with questions to keep him talking.  The more talking he does the more you know about him. 

3. Check the self-consciousness at home.  Remember: you should always live life to love life.  It's important not to stress and always have fun. 

And then, just to make sure I understood, he summarized things "in michelle terms":

1. [guys like girls with personality] let it flow.
2. [guys like girls that show genuine interest in their lives] fact.
3. [guys like girls who enjoy the simple things in life] keep it simple & fun.

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.