Dating Diaries: I Think The Problem Is More About Me Than The Ladies- A Single Dad

I’ll never forget when my friend Sarah sat me down many years ago to lecture me about my relationships with the opposite sex.

“Do you know how many girlfriends you’d have if you shut your mouth? You’re smart, sexy, funny, caring and interesting. You read more than anyone I know and you’ve traveled all over the world. However, your constant need to entertain yourself is your Achilles’ heel. You’ve got to learn to shut up. Also, it would help if you didn’t have such an obvious indifference to whether people liked you or not. Idiot!”

At first, I was shocked by her honesty but then I slowly realized that her points were completely valid. I did need to work on how I related to other people.

That lasted about two days.

Look, I know I can sometimes come off as a sarcastic prick who tends to use humor as a defense mechanism and frequently finds himself lapsing under the Mendoza line into the bush leagues of unintentional rudeness. At the same time, I think I may have some form of Tourette’s that has removed the filters between my brain and my mouth.

But it’s not that I don’t like people. It’s just that certain events have made me poignantly aware of how short life is and that I shouldn’t waste time with shallow idiots who make the Jonas brothers sound like Truman’s counsel of Wise Men.

Is it so wrong that I’d rather be alone than spend time with humorless people lacking in intellect, emotion, empathy or character?

I was thinking about this recently when it suddenly struck me that empirically I am a 41-year-old single father with a 5-year-old daughter.

Holy crap!

I’m an old dude with a kid and a weird sense of humor.

Ok, maybe I’m not old but I’m definitely ringing the buzzer on middle age.

Part of the problem is that in my mind I’m a much younger man. Unfortunately, I’m not. This, in and of itself, wouldn’t be a big deal if not for the fact that I would like to get married again and possibly have more kids.

And since there’s no way that I’m going to date outside my own age range, I’m thinking that I might have to start displaying a little more maturity than I did in my younger years.

Recent conversations with women are convincing me that this may be much harder than I realized and there remains a fairly decent chance that I will die alone.

Conversation No. 1

Woman: “Do you like to read books?

Me: “Immensely. Why? Are you reading anything interesting these days?”

Woman: “Yes! I just finished Twilight. I loved it!”

Me: “Me too! Didn’t you like totally cry when Dumbledore died at the end?”

Postmortem analysis: “As a general rule, I don’t date women who read children’s books.”

Conversation No. 2

Me: “Wow. You sure like flossing your teeth.”

Woman: “Yes, I do it after every meal. Don’t you floss your teeth?”

Me: “Religiously.”

Woman: “Every single day?”

Me: “Nah. Just Christmas and Passover.”

Postmortem analysis: “At the time, I just thought it was funny. However, friends tell me I was being glib and dismissive. Does it really matter? Could I ever be with a woman who was so obsessed with flossing that she did it publicly after every single meal? I think not.”

Conversation No. 3

Me: “Actually, I always thought WWJD meant ‘what would Jesus drive?'”

Woman: “Cute. Well, what kind of car do you think Jesus would drive?”

Me: “I don’t think Jesus drives. He just rides in the back of a giant Escalade.”

Woman: “Why an Escalade?”

Me: “Because everyone says Jesus is their homeboy and all the homeboys I know drive Escalades.”

Woman: “Don’t you think Jesus would be more environmentally conscious?”

Me: “When you roll with a large entourage, higher emission standards are generally subordinate to the need for third-row seating.”

Woman: “Jesus rolls with an entourage?”

Me: “Yeah, those 12 guys following him who keep asking him to turn water into wine.”

Woman: “You’re not a religious or spiritual man, are you?”

Postmortem analysis: “I know. It’s hard to believe I’m 41, isn’t it?”
It’s interesting being single at the age of 41.

When I was younger, I dated vastly different kinds of women because I wanted to expose myself to a diaspora of individual personalities. Now that I’m older, I tend to find myself far more selective. Or maybe the proper word is discerning.

Nick Hornby once said that it was no good pretending any relationship has a future if your record collections disagree violently or if your favorite films wouldn’t even speak to each other if they met at a party.

A small part of me tends to agree with this sentiment. Especially at my age, the idea of being in a relationship with someone who shares my interests and similar perspective on life is warmly comforting. I tend to be very passionate about the things I love so there’s a large part of me that wants to be with a woman whom when I read a great book, hear an amazing song, watch a deeply moving film or discover a new restaurant, I can run up to her excitedly and yell, “Look what I found! This is US!”

On the other hand, doesn’t every couple start off by talking about all the things they have in common? And if the relationship doesn’t last, don’t you just end up thinking about all the ways you were so different? More importantly, isn’t life much more interesting being with someone who not only has different interests but also brings a different perspective to life?

Does anyone have the answers to these questions?

When it comes to the subject of compatibility, I confess to being as confused as I have ever been. We get together with people because they’re the same or because they’re different, and in the end we break up with them for exactly the same reasons.

Now granted, there are many other aspects besides compatibility that are important to any healthy relationship. However, when you’re single and thinking about whom you’d like to date, compatibility tends to take on a heavier weight.

Honestly, I don’t know what the future brings for me and I’ll confess that there are times when this uncertainty makes me a tad nervous. I’ve always been fairly good at meeting women. At the same time, I’ve always been fairly good at being alone.

Maybe a little too good.

While I am an avowed romantic who firmly believes that no man is an island, I also find myself thinking more and more at this age that perhaps the ideal goal of a relationship between two people isn’t a merging of two individuals. On the contrary, maybe the healthiest long-term relationships accept that, even between the closest people, infinite distances exist and the key to happiness is to not only wholly love someone but also to be comfortable with the great expanse that inherently lies between you.

Then again, as another female friend tells me, maybe I just think too damn much.

What say you, my friends?

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