The best advice I ever got soon after my divorce came from a friend, who point blank told me “dating is a skill, and it is a skill you don’t currently possess.”  Now that may seem harsh, but she was right– I knew how to be a mom and wife, but I’d been out of the game for over a decade, and her point was it would take a while to get back in the groove.  Luckily, I’m a voracious reader and quick learner, so it did not take long to get up to speed on Dating in the 21st century, which I will lecture about next week.  Here are some other helpful tips I plan to share:

1. Be prepared to go on 20 bad dates.  When I first heard this, I thought WTF?  But actually, this is smart to set low expectations, then you can only be pleasantly surprised.  The point is to just think of dating as a journey, and don’t worry about the final destination.

2. Trust your gut.  If something doesn’t feel right, don’t force yourself to stick with it.  Dating should be easy.

3. Know your deal breakers and stick with them.  Don’t let someone try to negotiate with you to accept something you don’t want in your life.

4. Find your own happiness first, then love will eventually find you.  First, if you are still angry about the past, you will repel others.  Second, in moments of desperation we may try to convince ourselves to make certain compromises, and as we all know it’s never good to negotiate from a point of weakness. So get to a good place personally, then you will accept the love you really deserve.

5. Don’t take rejection personally.  You never know what is going on inside another’s head– whether they are busy with work, still getting over an ex, unable to commit to anything, or simply still processing their own past baggage, so “no” may not have anything to do with you, and all it does mean is that this wasn’t meant to be.

Now the worst advice I ever got ironically came from someone claiming to be a dating expert, who suggested that I may want to get my intellectual stimulation elsewhere.  While I am painfully aware that only about 15% of the U.S. population has a graduate degree, how can anyone possibly expect a professional woman to dumb-it-down on a date?  It’s not going to happen.  Here are some more useless tips:

1. Give it 3 dates.  Why?  What is the point?  If I don’t feel a spark after the first date, why should I waste any more of someone’s time, money or energy?

2. Maybe you are being too picky.  Okay so maybe I am choosy, but shouldn’t you be when you are contemplating letting someone into your life?

3. Let the guy lead.  Well if we were at a dance, I would, but if we are playing  20 questions, it’s a game and we are supposed to each take turns, and I am not going to respect someone who launches into a monologue or cannot hold his own around me.

4. Stop holding out for fireworks.  How is this possible, aren’t you supposed to be wowed by the person you choose as your partner?  I have tried to ride things out– 5 months, 10 months, 15 months, whatever at some point if the fireworks are not there it is just game over.

5. Don’t focus on the outside packaging so much.  Really? Easy for others to say when they’re not the ones going to bed or waking up next to that other person with a lovely personality.  Don’t get me wrong, character counts for a lot, but we are all visual creatures, and if you cannot get past the visual, then just stay friends.

Seriously, this really isn’t rocket science– boy and girl just need to meet (not online but actually live) for a real date.  If they click, they’ll eventually shag, and if that works out, they should have fun for at least a few months.  Eventually, inevitably someone is going to want more of a commitment, and either it will work or it won’t between two consenting adults that will lose their minds for some time while experiencing a crack-cocaine high stemming from their lust, and while they may be oblivious to the world around them, the rest of us will gaze half with envy, half with laughter thinking oh boy, here we go again with that crazy, stupid love.


By Regina A. DeMeo, Esq.