First Date, Part Deux – The Sequel!

After a successful first date and tons of texting for a week, we made plans to see each other again.  By now, I’ve introduced her to Mad Men, found out she has ice spheres for her cocktails and enjoys dressing up properly for a date.  She sets up a Mad Men themed date to showcase my suit and her in a dress.  On the way out, it’s raining…again.  As an after thought, I grab my umbrella to protect my suit.  We meet at the Melting Pot. I walk in and awkwardly fumble with my umbrella and go for a hug as she leans in for a peck on the cheek.  She’s wearing the reddest lipstick I’ve ever seen, but what I’m most drawn too are her gorgeous legs.

We finally get seated and have an amazing meal, complete with gin and tonics, followed by more hours of conversation.  My hand falls upon her leg, by accident of course, and it is smooth and strong.  This is getting serious.  We finally call it a night and as we step out, still raining.  For hells sake, will I never get to kiss this woman?!  I pop open the umbrella, walk her to the car and before she can get in, I pull her close with my free hand and kiss her.  Of course, it’s amazing.  I ridiculously turned on but cold and getting wet, so we say goodbye.  Of course, things went really well so I know this has at least turned into a trilogy.

First Impressions

We’ve all heard the expression, you find love when you least expect it.  It’s strange to actually live it.  As I have written before, my marriage of 15 years ended in divorce.  I then spent a couple of months retooling my style from frumpy suburban dad to less frumpy newly single dad.  After that, I boldly went forth into the dating pool.  After a decade and a half of being out and not having done much dating before I got married, I made a fair amount of mistakes, broke a few hearts and had my heart broken.  Overall the experience has been a positive one with lots of new friends and insights.

After my initial going out as much as possible phase, I settle down to just dating one person at a time.  It was too hard to keep all the details straight and felt serial dating just wasn’t my style.  I wanted to be able to focus on just one person and give them my full attention.  I did just that and had a girlfriend for a few months.  I initially wanted to bail early, but I thought that was just my own shortcomings trying to sabotage me.  In the end, I realized my initial gut feeling was correct and that I just didn’t feel as strongly as she did.  It ended painfully and I regretted having hurt someone, though it was never my intention.

I decided I was done for a while.  It was hard disappointing myself and others.  I went back to the dating sites I used to clean them up after months of non-use.  In the process I came across one that had sent me a little winky, smiley face and I had sent one back but had not done anything else.  The pictures were of this really cute girl, who was quirky, enjoyed dressing up for halloween and liked cats.  Meh, I like cats. So I sent her the canned questions thinking it would take a while to work through all those anyway and one of us would probably lose interest.

A week later, we met.  It was really cold and rainy and I almost didn’t go.  When I walked in, I stopped to survey the room, see if I could spot her.  I stood there for what seems like forever, then I see her wave, stand up and walk to me as I reach her, she opens her arms and says, “I’m a hugger” then embraced me.  Immediately I’m smitten. She’s more beautiful than her pictures, she’s open, and smells amazing.  We proceed to talk for four hours and had it not been arctic cold out when I walked her to her car, I would have gone for the kiss.  Needless to say, it was a fabulous first date and led straight into part two.


My marriage has ended after 15 years and now I have to get back on the horse, rejoin the race and see what’s out there.  I can say without a hint of irony that this is not where I saw myself at 40.  I was not especially good at dating 20 years ago, so the idea is a bit daunting.  However, being one that never backs down from a challenge,  I see this as an opportunity to correct past mistakes and finally find the person I am supposed to be with.

I approached this challenge like I do many others.  I took stock of my strengths and weaknesses, looked at what I wanted and then jumped in with both feet.  On the plus side, I look younger than I am, I’m fit and healthy, I dress well, have a stable job and very little drama in my life.  On the list of possible obstacles, I am the father of three kids, the divorce is not quite finished and I am still in the process of rebuilding my identity as a single man.

Since I’d prefer to be with someone that could eventually be my partner, I don’t think cruising bars is the best approach.  I joined a few dating sites.

  2. Plenty of Fish (POF)
  3. eHarmony
  4. Zoosk
To date, I have met women from the first three.  Zoosk seems to be the lest user friendly and begs for money at every turn.  Next is eHarmony that give you very limited choices, doled out each day a little at a time and goes wildly outside your preferred range. and POF have the best user interface, plenty of choices close by and most users have multiple pictures.
What I have learned in my short time.  Have multiple pictures of yourself and make sure at least a few are full body and recent.  Don’t stand in front of a mirror, don’t be shirtless, do not wear hats and no duck lips.  For both men and women, there are a lot of people putting pictures of themselves up from years ago.  Weight and hair color changes surprise you on your first meet.  Treat this a bit like looking for a job.  Know what you want, don’t settle for less and send out feelers as much as possible.  Network when possible, blind contact as needed.  The more your name and face are out there the better chance you have of being seen.

Have a thick skin.  You will face rejection…a lot of it.  Keep in mind, women have guys copy paste them all day long.  They may reach your message at the end of thirty and delete it without looking.  Or maybe you aren’t what they are looking for.  That’s fine, move on.  NEVER contact a person more than twice.  Once should be enough, but on that off chance it got nixed.  If a woman is gracious enough to to message you back to say no way, say thank you and move on.  Every woman has a story about saying no thank you and being verbally attacked for it.

In summary, know what you want, what you have to offer and put yourself out there.  No one is going to come knock on your door.  You will fail, a lot, but that’s fine because the payoff is worth it.  Don’t go looking for love, look for interesting people that compliment your strengths and weaknesses.  Most important, have fun.  Enjoy yourself even if it does not go the way you want.  It’ll at least be a story to tell your friends later.