Why Dating Is SO Confusing

This is not a tale of right and wrong. This is a tale of incompatible expectations and insufficient communications. If there is anyone to blame, I take 100% responsibility.

I met a woman on a dating site who I thought was awesome. Within 30 minutes of sitting down for a casual coffee (to which we both showed up early), she revealed her prior extensive drug addiction, which she battled while graduating with honors from a prestigious university (huge bonus points for delving into her shadow side at such a young age and coming out unscathed). And, we bonded over our love of music and our experiences in the music business. Since it seemed that both of us were excited for a more formal rendezvous, I proposed dinner a few nights later.

Again, we both showed up early and the conversation didn’t lag for one second. It felt as if we could talk forever about our unconventional lives, our mutual interests, our similar travels around the world, and our careers.

Then the check came. Being the male part of the equation, I reached for it — but not too quickly. It sat between us for a minute before I slid it slowly toward me and put a card down.

My new friend — who was definitely in favor of women’s liberation, women’s equality, women getting paid the same amount as men — did not motion her hands toward her purse nor did she say, “I’ll get the next one.”

Again, this is not a tale of right and wrong; this is a tale of incompatible expectations, insufficient communication, and maybe a tinge of hypocrisy of which we are all guilty.

If men and women are equal, then we have equal rights and responsibilities, correct? This implies disregarding our culture’s underlying myths of knights in shining armor coming to save damsels in distress and other chivalrous malarkey that feminists labored so hard to eliminate, right?

We continued to chat for another 20 minutes and then went our separate ways.

The next morning I texted to thank her for another vivacious conversation and invite her for a walk on the beach that weekend. She texted back that she was leaving for three weeks and we could get together when she returned. I wished her a pleasant trip.

Here are the subconscious messages that I received from the aforementioned snippets:

1. Not reaching for the purse or offering to get the next meal said, “I expect to be taken care of.”

2. Texting that I should leave her alone for three weeks said, “I’m fiercely independent. I don’t need you. I’m my own woman.”

OK, so you’re your own woman but you expect men to buy you dinner? Is there not a shred of hypocrisy or at least a mixed message there?

On Planet Ira, because men and women are equals, we both reach for our wallets. One of us says, “I’ll get this one,” and the other one says, “That’s very kind of you. Thank you very much. I’ll get the next one.”

But isn’t this a problem inherent in the system? Despite wanting so much to be loved unconditionally, we only have tools and symbols to convey love conditionally (because we’re successful, smart, sexy, rich, pretty, articulate, independent).

Do you not see these antithetical messages in your own relationships? Don’t the conventions of courtship make us all hypocrites in some way?

For those of us who are not psychic and aren’t dating someone with psychic capabilities, the only solution is to communicate clearly and honestly so that expectations don’t wreak havoc on our lives.

On the other hand, isn’t authenticity often unromantic, and even a turn off? Particularly for men who are taught to create invulnerable facades and not display vulnerability?

And isn’t navigating subjects — particularly when trying to start a new relationship — such as sex and money usually awkward and painful?

When did something that seems so simple become so complicated?

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