The Feast and the Famine

Q: Personally, I am getting frustrated with the whole dating, search thing. Don’t know what to do, and need some advice. I am 53, divorced 3 years+ but don’t want an old grandma girlfriend, rather, prefer women a bit younger, say in mid 30′s to lower 40′s as long as they are mature, like to have fun but can appreciate a good man and what he tries to do for her and the relationship. My only “serious” relationship after my divorce went south and she broke my heart after falling hard for her. She just didn’t turn out to be as serious or committed to the relationship as I was or wanted her to be. I gave it a really good try, helped her out of messes several times but even though we are still “friends,” can’t see trying again. Any ideas? – Stumped

A: Of course, but you might not like them. Because it’s late and I’m exhausted, I apologize in advance if this comes across as extra-snippy, but you need a bit of a reality check here before you can expect things to change.

First of all, it’s terrific you’re looking for something that will last. But you’re looking in the wrong places. Shallow as this may sound, women in their mid-30s generally aren’t interested in committing to a 53-year-old man unless he looks like George Clooney or has the bank account to match. They don’t want an old grandpa boyfriend – sound familiar? I’m not advising you to hit the bingo parlors or anything, but stop limiting your dates to such a younger set and I bet you’ll see your luck start to change immediately.

I’d also suggest lightening up a bit. I get that you want to be valued for the good guy that you are (and I’m sure you are). But all the pollen in the air doesn’t quite overpower the slight whiff of desperation in your letter, what with all the talk of being “committed to the relationship” and “falling hard” and playing the role of rescuer over and over. Yes, for many women, the Holy Grail is finding a guy who actually wants to commit – but falling all over yourself trying to show us how eager you are to be that guy is the surest way to send us packing.

Q: I always enjoy reading your words to those of us out there in the dating pool, and now it’s my turn with a question. In the past week I had two amazing first dates with two extraordinary women. Both are intelligent, very well-educated and we had a really good time.

We connected online and in person. I’m going on second dates with them (separately of course) and the one thing I’m concerned is not leading them on when fully dating the other one. I also don’t want to hurt them. What would be your suggestion on how to handle this? By the way, I’m not looking for a one-night stand, it’s for a long-term relationship. – Help?

A: I got to your letter as quickly as I could, and I hope what I’m dishing out here is still applicable – i.e., you haven’t scared either of these two ladies off. These critical early days are all about nurturing the spark – not blowing so hard on it that it snuffs out.

You, my friend, sound like a prime candidate for Premature Emotionation, an affliction many men unknowingly suffer from. While a guy spouting off too early below the belt is indeed troubling, just as potentially damaging is spouting off too early from the mouth. As in, telling a woman in your first or second date that you’re looking for a long-term relationship. Which I sincerely hope you haven’t done yet.

As I told the letter-writer above (do you guys know each other, by the way?), I think it’s great that you’re looking for something substantial. But you’ve got to ease up on the reins a bit and see where things go organically. When it comes to exclusivity, here are the unwritten rules: Until it’s talked about, it shouldn’t be assumed, and it should never be talked about too early. It’s just as feasible that these gals are enjoying the feast – i.e., dating multiple people – just like you are. So don’t assume you’re the sole dish on their menu, either.

On that note: If, by “fully dating,” you mean “sleeping with,” then ideally you will have narrowed it down before then.

So, just to make sure you don’t come down with Premature Emotionation, I’m making some strict prescriptions here. First of all, keep dating both these girls; a front runner is likely to emerge soon enough. Second, when you do narrow it down, enjoy that buzzy initial phase without worrying too much where it’s all going. If it’s going somewhere good, soon enough that mystery will be replaced by familiarity – and then you’ll be writing to me about how to get the spark back.