Top 10 Worst Dates (#2/Runner-Up)

    It was a close call between #1 and #2 worst dates of all time.  Sliding in at second place is my memory in Chicago.

    I had a series of unfortunate events that led me to need to get out of town for a while.  I had been talking to a guy in Chicago.  I will admit there was a little romance brewing – and this was in the day of Meg Ryan and Tom Hanks (Sleepless in Seattle).  No woman my age who saw that movie back then didn’t at least secretly entertain the idea that such fairy tales, though few and far between, were possible.  So, my folks agreed that I need a break from the chaos in my life, and bought me  ticket to meet this stranger that I had come to care about.

    He had sent many pictures, and he wasn’t the hottest thing I’d ever seen, but he seemed really kind.  He often mentioned how people always told him that he looked like Chuck Norris.  Seeing his photos, I thought it was a pretty accurate assessment.  He had a tween daughter that we talked about a lot, so I felt like I already knew her.  His ex-wife (her mother) had left them both to pursue a life of drugs and booze with her boyfriend.  There’s always two sides to every story, so I put it in the “who cares” category.  The daughter had mental health issues, including anorexia.  So sad.  I wasn’t expecting to step into a fairytale, but at least it was not my problems here.  Anything was better than being here.

    I arrived at O’Hare Airport and was greeted warmly by my online romance.  I was thankful that he didn’t lie about he height, weight, etc.  No words were spoken, just a giant hug.  He showered me in compliments from the moment we met, “You are far more beautiful than your pictures,” “You have amazing legs,” “You are so gorgeous,” “I could not sleep a wink last night knowing you were arriving today.”  Men must be reading all the Women’s health magazines, because they are starting to sound more and more like what we want them to sound like.  I hate it…but I suppose it was nice to be appreciated.  His daughter greeted me warmly, too.  She was the skinniest girl I’d ever seen.  It was very alarming.  She had a daunting look, kind of hollow.  I knew that this was a lot of pressure for her and became acutely aware that I had to be a friend, not a girlfriend, for the length of my visit.

    We got to his full sized custom van with no a/c…it reminded me of the A-Team in a funny way.  But hey, who cares.  He was really sweet and just a gentle guy.

    I hadn’t made much firm eye contact, but noticed that when he spoke to me, his glance would turn away.  Maybe he was shy?  Uncomfortable? Nervous?  I couldn’t figure it out, but tried to ignore it and hoped it would change.  On the drive back to his apartment, he told me about every site to see between O’Hare and his place.  He talked constantly.  Men don’t usually do this in my experience…ugh.  I was really tired – I had the red eye flight and just wanted to sleep…but stay in good spirits, I am a guest in their home and had tremendous appreciation for their generosity and hospitality.

    As he spoke, I watched him in the rear view mirror each time he turned away.  Now it all made sense.  The guy was missing half of his grill.  Oh man.  I typically don’t judge people on looks.  There are so many things that we cannot help, and I know dental expenses are high and a lot of folks do not have the blessing of dental insurance.  I get it.  I did my best not to call attention to what I knew he was hiding, which made me stare even more I’m sure.  My biggest issue was that I was sure at some point during this visit, he’s going to try to kiss me.  Yikes.

    My plan: Keep the daughter around as much as I can.

    Night one went well – no mug out sessions or anything of the sort.  We played Scrabble and talked a LOT, all 3 of us.  I pretended to fall asleep on the couch.  He was so kind – he tried to wake me up to go the the bed and he’d take the couch.  I shrugged him off and said that I was too exhausted and would be fine there for the night.  I really didn’t want to get up, but it was for more than being just sleepy.

    The next day, we hit Chicago full force.  I LOVED this city.  I had so much fun at Navy Pier, the Observatory, Route 66, the pizza joints, the bars, and I even took my picture in front of the fountain that used to show up at the beginning of the TV show Married With Children.  Sears Tower was really neat – I did the whole Ferris Bueller thing where then leaned over the rail and placed their head against the glass and looked down.  I was a total tourist and didn’t care.  I had a great time.

    I began to see past the severely neglected grill of my host, and even though I had affection for him, I just could not click to the romance thing well at all.  It is a very awkward place to be in.  There’s no going home, no calling a cab – my plane wasn’t leaving for a few days, and this was my home for the next few days.  Plain and simple.

    He’d tried to grope, paw, and smooch here and there, and I would commit to an occasional peck, but resorted to the, “Not too much, too fast.  I’m a proper southern woman” routine.  He accepted it, but surely he didn’t like it.  Still, he was seriously an amazing host, and very clean.  He was attentive to me, his daughter, and never shut up.  I had to go to public bathrooms frequently just to have 5 freaking minutes of silence.  And I’d never seen a guy with so much hair product in his bathroom.  But, he did share the bathroom with his daughter, so that explained that.

    The day before I had to leave, he gave me a really gorgeous lingerie set from Victoria’s Secret.  He nailed the sized perfectly and it was certainly flattering and sexy – but the robe made it okay to wear around his daughter.  It was actually my favorite piece I think I’d ever had.  He did good – but how many guys can look at a fully clothed woman had know her bust, waist, and hip size so perfectly?  It was rockin’!

    I wore it in the hotel room that night – we had finished up my visit with a trip to Six Flags Mid-America.  Had a great time, and was wore out.  We had his sweet daughter in tow, so I kept it modest and worse the robe at all times, even in the bed.  He leaned over before we killed the lights and said, “I know why you wore that, but we can’t because my daughter’s in the room.”  Holy cow.  Seriously?  I was wearing it because it was my last night there, and felt it appropriate because they picked it out together and thought I would show my appreciation – not because I wanted to fool around with his kid in the room.  Perv.  Still, you have to admit, that’s amazing restraint for a guy.

    The next day, it was time to go home.  I wasn’t upset by it, I was ready to go home to my life.  I knew that I’d never see him again – it just wasn’t going to work the way I knew he wanted it to work.  He was dropping the “L” word on the way to the airport.  ARRRGGGHHH!  This poor guy.  I paid for as much as I could afford of my own meals, tickets, and expenses.  I tried to give him gas money, but he wouldn’t take it.  I knew he really liked me, and from what he said, he thought he loved me.  Honestly, I think he was enamoured, but love?  No.  I think, like me at that time, I was in love with the idea of being in love, and was looking to take anyone and fit them into my idea of love. It was all completely wrong, and it had major potential to be destructive.  It wasn’t what I thought it’d be – maybe it was teeth, maybe it was that he was shorter than me, or maybe it was his catering to my every whim and seeing how he ran on pure nervous energy.

    At the gate, we hugged, and kissed (the peck).  I hugged his daughter.  I knew something was seriously screwed up in her life.  Someone had just messed her up, and I wanted so much to take her home.  She was hurting in a major way.  She rarely ate, and she was so frail.  It broke my heart.  But in my mind I knew I was no more ready to take charge of another life when mine was wreck all by myself.

    I arrived home and told my folks what all my few days in Chicago involved.  They were sort of disappointed for me, but at the same time, I am certain they were utterly relieved.  I got home and had 14 messages awaiting me.  It was late, I’d call him the next day.  I turned the ringer off and went to bed.

    I awoke to 28 messages, 27 of which were Chicago.  I called him, and it was if I were talking to a woman.  “How was your flight?  Why didn’t you call when you got in? Did you get my messages? What’d you eat today? Where have you been?”  That pretty much sealed the deal for me.  Our conversation took a nasty turn as we discussed our future (or lack thereof).  He insisted I was moving in with him, and he had firm plans about how I was going to raise his daughter and not work.  It was like Mr. Hyde had reared his ugly head.

    I began to explain that I sincerely appreciated my visit, and thought he was a better host than my girlfriends I had.  That turned into how I wasn’t ready to make any rash decisions and that I just wasn’t on board with this plan.  I didn’t love him, and wasn’t really feeling any sparks.

    He began to tell me that he was a cross dresser and that he had taken my dress from my luggage the day before I left (I wore a cute short skirt and top to Chicago because I left right after I got off work that day).  I really liked that outfit, but I guess it was a good trade for the lingerie.  Then he said he was sending it to me because it was a little small, but that he was keeping MY SHOES!  Ugh.  There went a cute pair of shoes, too.

    As for his daughter, well, he hypothesizes she’s a mess because of her mother.  Well, as true as that probably is, I am sure that dad dressing like a woman and bringing home male dates didn’t help much either.  Oh yes, he slept with men!  I had never been more thankful for playing the “good southern woman” role.  I had never been happier to not kiss someone in my life.  My folks laughed hysterically when I told them.  They couldn’t believe it.  The guy was already a not-so-attractive man, and he was going to be a woman?  YIKES.

    I hope my heels helped his cause, and I still feel I got the better deal.  I know that lingerie helped my cause.  But in all seriousness, I so wanted to get his daughter out of there, but she had no where else to go.  She was so frail and hollow.

    Funny side note – I actually had met another guy from Chicago after this who came down to visit.  Had an amazing time and he was a really great guy.  Unfortunately, he was in the military and got stationed in Iraq.  We wrote emails and things, but eventually it all faded out.

    Wow.  I was seriously insane and made some terrible decisions in my single life…but don’t go up to bat if you don’t intend to swing.