My Blind Date with “Conan O’Brien”

FINALLY! The dating floodgates have opened and now, I practically need a secretary to keep my appointments straight on my calendar!  Where have these guys been?

Jeeze! It feels like I have been on a dating dry-spell for years, and now I’m getting bombarded with suitors?!  It must be my new online dating profile.  Either that, or the Dating Gods are now smiling down upon me for doing something right.


I’m not going to lie, there is still that residual energy…thoughts…whatever you want to call it, regarding DC Dude yet, I am determined to move forward. Even if I have to date everyone in New York City!  Ha!

So, the other day, I got home and I spotted my neighbor, John, standing outside his house smoking a cigar.  I like John – he’s in his 60’s and just a class act – happily married, well-traveled, and just has a wealth of knowledge to share.  (Plus, he told me I can take out his BMW M3 whenever I want to – and you know how I love my fast cars…)


As I was getting out of my car, I noticed John ushering me over and, as usual, we start to chit-chat.  He tells me that he just came back from a two-week trip to Italy with his wife and a good friend of his who he considered to be “like a son.”  He tells me all the fabulous things they did in Italy, all the while giving me the hard sales pitch on his friend.  From time to time, while describing his friend and his two-week long tour of Italy, he’d turn his head, take a puff off his cigar, and in very contemplating manner, blow the smoke up in the air very, very casually.  I could tell he was contemplating something.

“You know, my friend is single, and I actually brought you up while we were in Italy.  I really think the two of you should meet.”

My first knee-jerk reaction was of course, “How tall is he?”  John looks up in the air, scratches his beard and showing me with his hand he says, “I think he’s about 6’1″.

(More than likely, the guy is only six feet tall which, still isn’t bad but, *wrinkles nose* I would prefer taller.  I’m 5’11”, I need a tall man.)

As our conversation continued, I’m thinking, “Do I have enough time to squeeze in another date?” My dance card was getting full at that point.  Match from Hell was paying off – I had three guys on the roster already:

1. Landscape Guy
2. Interior Designer Dude
3. Swedish Psychologist Dude.

But, what the heck?  Why not?  What’s one more date?  What’s one more guy………?

I realized after John’s great sales pitch that I was going to have to give him my phone number.  I grabbed a scrap of paper out of my bag, wrote down my digits and handed it to him.  Reading my phone number out loud, John seemed quite pleased with himself.

As I was walked away, he added one more thing, “Oh, by the way, Carrie, my friend has three children.  Fourteen, twelve and nine.”

Fourteen, twelve and nine……….

Suddenly, in my head, I became Julia Roberts in the movie “Stepmom.”

OK, well John….that would be an important piece of information to give me before I agreed to meet your friend.  Three children?  That’s a lot!  Not that I don’t like kids, but that’s definitely “instant family” right there.  Kinda scary, if you ask me!

Walking over to my house, I yelled back, “Thanks for that information John! Hey, by the way, what does he look like?”

Confidently, he says, “He’s looks like Conan O’Brien,” waves good-bye and walks into his house.

Wait, Conan O’Brien?

My blind-date called me two days later and, after a nice 20-minute conversation, we made plans for a dinner-date the following night.

The night of my blind date, I got home and tried to talk myself out of going. We all know that blind dates are disastrous…what was I doing?! He’s probably going to be fat and short – oh, my God, this is going to be painful!

By the time I had was ready, and had bitched several times why I should be canceling my date to my roommate, the doorbell rang.

Right before I answered the door, I took a deep breath and said a small prayer.  I decided that whatever the guy looked like, I was going to be gracious.

When I opened the door, what I discovered was not a look-alike of Conan O’Brien, but a very handsome man!  Hell, I practically fell over because my blind date was hot!  Not quite six-one, but…


…we all knew he was only going to be 6′ anyway.

Dinner was very enjoyable. He spoke immediately of his three children – two boys and a girl. He had married his high-school sweetheart, and had been divorced for 8 years – simple enough.  He was in sales so he had no problem holding a conversation with me.  I was thoroughly enjoying my date.

He was definitely easy on the eyes.  I couldn’t help but notice that he was a really good-looking guy with a square jaw and looked more like Ed Harris (with a full head of hair) than Conan O’Brien for damn sure.

Hello!  Ed Harris!  Meow!

I have always been a sucker for that strong, square, Irish jaw….


Wait, my father has the same classic, Irish look – small nose and strong jaw.


Moving right along…

I’m two glasses of red wine in and we are onto the subject of last names. I happen to be really be fond of my last name. My date seemed to like it, too. Then, he tells me that he’s actually not Irish, but Scottish…and said his last name was “McSomething.”


La-la-la…I’m feeling no pain…Scottish…Irish…whatever, it’s all the same to me (seeing I’m both as well). I take another sip of my wine, but stop mid-sip and blurt out, “But, wait…I thought your last name was O’Brien…”


For the love of God, in my hazy red wine moment, I couldn’t think of where I got the idea that his last name was “O’Brien.”  I was drawing a blank, and it didn’t help my awkward moment when I started mumbling my own thoughts out-loud.  Ooops!

Once I realized my error, I was quick to switch the subject, never knowing if my blind date knew his friend, John, described him as Conan O’Brien…

Despite my big dating faux pas, we ended the evening with a little kissy-kissy make-out session in the car when we said good-bye when he dropped me off at my house.

(By the way, he was a good kisser.)

The following day he sent me a text, “What a good time, I enjoyed my blind date!” I responded back by saying basically the same thing, but I didn’t hear from him after that. OK, fair enough – I had fun, and this is what dating is all about.  At least, that’s what Nathan, my brother, keeps telling me…

Well, Nathan, I had fun!



Interior Designer Dude

Hi there! You have a lovely profile and, needless to say, beautiful pictures. While I don’t quite hit your age threshold, it seems we otherwise share some common ground – I’m English and Irish, love NPR, Italy, and country living (among other things!)

In any event, your profile really resonated with me and I felt compelled to write. If you like what you see and think we have a chance at an interesting conversation I’d be delighted to hear from you.


That was from Interior Designer Dude. Yes, a “little older” at 52-years old, but he must have strong Irish genes because, MAYBE, he looked 42. Good for him. I figured it must be all that good country living.  My kind of guy.

I read in his profile that he lived in a lovely area, right across West Point, NY on the Hudson River.  Just my luck, it happened to be the next town over from where The Architect lives. (Hopefully, we won’t be running into each other, well actually, I’d love to run into him, because I have a few choice words I’d like to share.)

Interior Designer Dude had a great profile and pictures. I wrote back to him immediately, and after a few emails one Saturday afternoon, he asked me if I would like to meet him for a drink that night.  Why not?  I’m always one for spontaneity so I said yes.

I let him do all the planning and he did a good job of it. He picked out a place that was equal driving distance for the both us. (Points for being considerate.) He chose a new place call Axia in Tenafly, NJ.

I walked in and spotted him immediately at the bar. (He’s hard to miss with his white hair.)  We both ordered a glass of red wine and immediately started talking, which I noticed that talking with his was effortless.

I learned he was divorced with a 6-year old daughter and owned his own interior design firm. Originally, he said he had started out as a party planner in New York City, and discovered a talent and passion for design. God bless him, because someone has to plan parties and I was glad it wasn’t me. Because, if I had to plan someone’s party, I would probably break out in hives!

Overall, it was a nice evening with him. I enjoyed myself, and when we decided to leave, he asked me if I would like to see some of his work that he had in his car. Of course, I did!

I slid into his velvety leather Mercedes passenger seat; he pulled out his Mac computer and started showing me pictures of his work. It was very classic – very Architectural Digest.

Statuesque at 6’3″, Interior Designer Dude was elegant in a very refined way, but at the same time youthful in spirit. Had I seen him in the pages of a Banana Republic catalog before? He never mentioned modeling, so maybe not. Regardless, he treated me with the utmost respect, was cognizant of my personal bubble and didn’t try to molest me at the end of our date.


The kiss good-night was brief – just one kiss, and I was home before midnight. Again, points for him. As a general rule, I find that most guys will ask me to text them when I get home. However, he didn’t say anything to me when I left, but five minutes after I crawled into bed…

Interior Designer Dude: Did you get home okay? Thank you so much for tonight. You are wonderful, Carrie, and I’m smitten, what can I say? Sweet dreams and I hope to see you again soon. There you have it.  An easy date, with a really nice guy.

Finally!  I’m attracting the nice guys instead of “That Guy” or “Bad Boys”!

That was all less than a week ago, and already he’s asked to see me again. So, Thursday night we are going out to dinner after work. He offered to cook me dinner at his house, but I think that it is way too soon to be alone in his house. I don’t care how nice he is – it’s too tempting.  Guys seem to lose their composure when they have me alone at their house, so I told him he can show off his culinary skills at another time.


Until then, I have other dates to go on, but he will definitely get a second date!