OK, since I haven't been on a decent date in ages, I have decided to dust the cobwebs off some of my previous dating stories and share them on this blog. Yes, my bad dating history is extensive and dates back for years.
Back in Chicago, I was set up on a blind date with a guy by a mutual friend. All I knew about him was that he was over six foot tall and worked in TV news (not on camera). Our date started with cocktails at Rock Bottom, killing time before our dinner reservation at 9pm at Green Dolphin. So we're sitting at the bar having our first drink when a bunch of guys at the other end of the bar walk over, maneuver between us, and start trying to guess my ethnic background (This happens to me a lot...I'm pretty sure it's just a cheesy way for guys to approach me, but the dialogue gets old fast. They never guess Filipino. How can that be?!?). Anyhoo, these randoms just keep chatting it up. I tell them I'm on a date, introduce said date, but they still hang around. By now my date has been pushed about 4 chairs down as the randoms have made themselves comfortable.
One of the randoms (we'll call him Stalker Boy) asks me out. As I make note of the rather large, gaudy wedding ring he's sporting, I inform him that I'm on a date and he's married. I guess these were technicalities for him. I make small talk with Stalker Boy while trying to extract myself from the situation.
Blind Date Guy and I finally leave the bar and go to Green Dolphin for dinner. In the middle of dinner the hostess comes over to me and asks if my name is Eileen. It seems I have a phone call. Once I walk over to the host stand to take the call I find I'm talking to Stalker Boy. He just wanted to let me know much he enjoyed meeting me and was checking to see if I had changed my mind about going out with him (during my chit chat with Stalker Boy at Rock Bottom I happened to mention where we were having dinner, so he knew where to find me). Weirdness.
Dinner chugs along. We decide to get an after dinner drink at this place next door to my house. I make a quick stop at the ladies' room since I had broken the seal. As I'm walking to the bathroom door, someone grabs my hand and says "Where you going in such a hurry?" I look up and see...Stalker Boy. Needless to say I skip the potty break, grab Blind Date Boy and break a sprint to the valet. Blind Date Boy wants to confront Stalker Boy, but I recommend against it.
We go to the bar next to my house. It's got a private VIP room on the top floor. We use my card to get in and I make a dash to the ladies room, since I didn't quite make it at the last spot. I get delayed in the potty talking to a friend. When I walk out of the bathroom Blind Date Guy is standing there with a startled look on his face. A little too pale, even for a white guy. It seems he met my friend Michael. Well, during the day he goes by Michael, mild mannered boat salesman. At night he becomes Michelle. Michelle was almost a woman...and loved her new breasts...and was showing them to everyone at the bar. I have seen them a hundred times, as she tended to whip them out every time I saw her. So I guess the whole man with a penis and breasts thing thew him off.
Settling in with a cocktail at the bar, I think we're finally going to get to relax. In walk Big Skinny, Uncle Frank and Simon (names changed to protect me). These guys were good friends of mine, taking me with them to "lunch meetings" in Little Italy about once a week. They wore suits every day but didn't go to an office. They carried guns that I was never supposed to ask about. They took meetings at which I was never to remember the conversations. I had a great deal of respect for these guys and was smart enough to know not to ask any questions. After a little hug hug, kiss kiss, Big Skinny, Uncle Frank and Simon have a chit chat with Blind Date Guy that I didn't get to hear. Lots of whispers. They finish talking and Blind Date Guy grabs me and drags me out of the room, down the stairs and out the front door of the bar. Again, back to that super pale, kinda panicked look on his face. He took one look at me and said, "Do you know who that was? Do you know what they do? Do you know they're in the Mafia?" I put my hand over his mouth and try to stifle the rambling. Of course I knew! I just didn't talk about it. Guess their private conversation centered on a couple of veiled threats centered around what would happen if Blind Date Guy didn't treat me well.
By now I am sure Blind Date Guy had had enough. You'd think this guy would break a sprint for the car, drive away and never look back. You would be wrong. I dated him for years. Even got engaged. And planned (and cancelled the wedding). Twice. Unfortunately, years of my life that I will never get back.
Thursday, May 28, 2009
Wednesday, January 28, 2009
The Pinhead
So last week I went on a date with a guy that I wasn't sure about from square one. I spoke to him a couple of times on the phone and there was something I couldn't pinpoint that was off. He was kind of soft-spoken (and you know I am not), so I thought that might have been it.
We met for drinks after work. Voice was still very soft-spoken and now he had some sort of speech impediment. Not sure if it was a lisp, he was effeminate or his southern Illinois accent was getting in the way. But one way or the other it was hard to get over. From the neck down he was smokin' hot. Very built, huge chest, giant biceps. From the neck up he had the head of a premature baby. As in his head was waaaaayyyy too tiny for his body. As in the attached picture. But in real life.
Since I can't get over all of these things (one thing maybe...all together, not a chance), I decide I won't see him again. Of course he calls every other day. Still.
Wednesday, December 31, 2008
Fancy Pants Man - Part II

So any time I talked to Fancy Pants Man on the phone and the topic of cars or driving came up, he would refer to his car as a Pinto. As in "I drove my Pinto to work today." or "I had to fill the Pinto up with gas.". I guess he wanted me to ask what kind of car he really drove. Anyone that knows me knows I don't care about cars at all. I am not a good driver, and cars are meant to get you from point A to point B regardless of whether it's a Dodge Dart or a Maybach Landaulet.
Anyway...when we went on our date we drove separately (he was annoyed by this, even after I explained that I would never get in a car with a stranger...a great life tip told to me by my mom when I was a child and still pertinent today). We had decided to go to a sports bar after dinner to watch the end of a football game. I handed the valet my ticket first. While the valet was getting my car, he was giving me directions (Follow my Pinto and when my Pinto turns in three blocks, follow it. Park by my Pinto). When the valet returned, he looked at me, looked at my car, looked back at me and says "That's your car?" I answer, "Yes. I'll have my Pinto follow your Pinto." For the record, I drive a black Mercedes sedan, which is not meant to brag, but will become relevant soon.
So the valet goes to get his car as we're having this conversation. His car gets pulled up and I'm waiting for a BMW Z4 or a Lamborghini Gallardo Spyder or something of equal awe factor. The valet pulls up with a Lexus SUV. And not the big one. Just the standard soccer mom SUV. Not that there's anything wrong with a Lexus SUV. But if you're going to pimp me all week about your "Pinto", your car had better fly or drive itself. And a Lexus SUV does neither.
Wednesday, November 26, 2008
Fancy Pants Man

So last week I went out with this guy. Why will I never see him again? It was his jeans. That's right...his jeans. The man wore jeans with stuff on the back pockets. We're not quite talking rhinestones, but there was definitely more design stuff on his back pockets than mine. Maybe I'm old-fashioned, but I have a staunch belief that a man's jeans should have nothing on the back pockets (which means you got them at the Gap or Banana Republic) or have that familiar stiching indicating you're wearing Levi's. A man should not be wearing True Religion, Rock & Republic, Chip and Pepper, Earls or any other brand (unless they have plain pockets, of course).
OK, so his jeans weren't quite this decorative, but it was close. Very close.
And there was also the issue of his Pinto, but that's for another post.
Monday, October 27, 2008
Forehead Kisser
So a while back I went on a date with this guy who is known about town to be a playa. That's right...playa with an "a", not an "er". Granted he's super good looking, has a great job and is loaded. He has dated two or three of my friends, none of whom had stellar commentary about him, so that probably should have been my first sign.
Anyway, we went on said date (which was non-discript and rather vanilla, so I'll spare you the boring details). At the end of the date, he walked me to my car. At the end of a first date I have had men shake my hand, try to high-school make out, Grandma kiss, etc. But this is the first time I had someone kiss my forehead. You got it...my forehead. Which would have been great if he were my dad, or we had been dating for a long time. But it was a first date. Come on now! He was about a foot taller that I am, so I thought maybe it was a logistical issue and he would go in for a second attempt. Nothing.
Since he never called me again, of course I had to start telling people about him. A couple weeks later I was at a private party happy hour deal, holding court, telling my forehead kisser story to about ten people. As I am standing there finishing up my story I say, "...now ladies and gentlemen, please don't all turn around at once, but the Forehead Kisser has entered the building." You heard me...he had come to this happy hour thing with one of my neighbors. Naturally, all ten heads turned around at once and stared at him. He was so uncomfortable he spent the rest of the evening running away from me. So mature.
Anyway, we went on said date (which was non-discript and rather vanilla, so I'll spare you the boring details). At the end of the date, he walked me to my car. At the end of a first date I have had men shake my hand, try to high-school make out, Grandma kiss, etc. But this is the first time I had someone kiss my forehead. You got it...my forehead. Which would have been great if he were my dad, or we had been dating for a long time. But it was a first date. Come on now! He was about a foot taller that I am, so I thought maybe it was a logistical issue and he would go in for a second attempt. Nothing.
Since he never called me again, of course I had to start telling people about him. A couple weeks later I was at a private party happy hour deal, holding court, telling my forehead kisser story to about ten people. As I am standing there finishing up my story I say, "...now ladies and gentlemen, please don't all turn around at once, but the Forehead Kisser has entered the building." You heard me...he had come to this happy hour thing with one of my neighbors. Naturally, all ten heads turned around at once and stared at him. He was so uncomfortable he spent the rest of the evening running away from me. So mature.
Wednesday, October 15, 2008
Yikes! Stalker Boy update!!!
I went out with this guy some time in July and I had to involve the police in getting rid of him, so I have been pretty happy that I haven't heard from him. Until today.
I got an email from him that said:
I got an email from him that said:
Hi. At least read my email. Thank you. Hopefully you remember me.
I certainly remember you. I thought you were very pretty, smart
and easy to be around. That's important. Somehow (unknown to me),
I managed to offend you. I thought we had a good first
encounter at Bonefish remember. We all have some type of shortcoming.
Maybe we could try again. I think you're great.
At least give me a chance.
Do I remember you? Of course, I remember you! You called me 15 times a day! You own not one, but two escort services! You're still married! You're hard to forget. And you won't merit a response to your email.
Wednesday, October 8, 2008
Another update on my self-inflicted wound
This is what it looks like when you take off your bandages off your second degree burns. Nice scars, huh?
Subscribe to:
Posts (Atom)