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Love Walter: Oh Cupid, Why do You Keep on Calling?

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Dear Walter,

I’m dating again. Putting myself out there with the promise that someday I may find the elusive one. But let’s not get carried away. I’ve been on some interesting first dates in the past, and I wonder what should I expect for the future?

I’m dying to know your thoughts. 

—Dating Again


Dear Dating Again, 

First dates are like to first mistakes that decide a relationship’s fate. Stupid Cupid called me again, this time telling me to meet a man in a mall. A who?  Malls are for normal people. The idea of going door to door indoors seemed archaic. After two martinis and a promise of the free meal, I got dressed to meet him. This would be our first date. I didn’t know what to expect. 

It felt like 2002 again. I met him in front of a Nordstrom, and I hoped it was the other guy. He seemed more my type, looking hood in a Burberry t-shirt and Nike rubber slides. But do I want my guy sliding around Pentagon City on our first outing? And who the hell still wearing Burberry? But I wondered what was hiding underneath that plaid tee.

Instead, he appeared dressed like a tourist in a ball cap and a backpack. While exchanging introductions, I noticed his initial social awkwardness. When he smiled half his teeth were gone. Somehow his missing teeth were missing from his profile picture. There was a tinge of disappointment. Cupid you got me again. 

I decided to make the best of it. He guided us to the Windows store, which was like the Apple store minus the Apple magic.

Our sassy salesperson was a blond black guy with blue contacts. He was a ball of contradictions masquerading as high self-esteem. Working retail at 59 was not exactly the high life. “I see you found your new best friend,” he said while cracking a half smile. Someone should tell him not to smile. I sipped New Amsterdam Apple with Sprite from my McDonald’s cup. I helped him select a $99 mini tablet. Apple has been scamming me for years. 

We stood and watched the virtual reality machine, which looked intense. He wanted me to try it. I declined. We sat instead and talked tech to a sales girl.

We meandered around the mall for another hour until it was time to eat. He decided on Chipotle and I tagged along. He ordered his food to go, and didn’t even offer to pay for mine. 

At this point, I’ve lost hope. I took a to-go water cup and filled it with Vodka. I sat there wondering why I even left the house. But at least I put myself out there. We ended our date with a fist bump. Our fists connected like homeboys. I missed the Real Housewives of New York finale for this.

I don’t care if he ever calls. 

Sometimes a match is not a match, and coping through vodka in paper cups isn’t exactly my idea of the best time. But during those days, during those troubled times, vodka went with everything, spicing up ordinary drinks in public places. 

Yep, I’m classy. 

It’s just awakened trying to vibe with someone new with or without cocktails. Some people like to have first dates in the comfort of their own home. But those “dates” if you would call them that are often too comfortable and too casual. And with cocktails, sex is around the corner. What the hell it could be nice, especially twice. 

But back to knowing better and thus doing better, you should meet him somewhere public. I recommend a restaurant. That way you can flirt and feast. Just be careful not to make it a job interview with cocktails. There is nothing more annoying than being darted with too many questions. 

You got this, make it happen like Mariah. I wonder how’s her dating life post billionaire? Well that’s rich people problems. It’s fun to dream but sometimes it’s best to be steeped in reality. Even if your date is shitty, at least you’ll be able to enjoy a good meal. Could you imagine? I watched my toothless date eat Chipotle? 

It surely can’t get worse than that. 

As always, enjoy your life responsibly. 

Love, 

Walter


Got a question? Email your letters to [email protected]

Walter Reed

Walter Reed is writer and advice columnist on love, lust, and life. Romance is his day job. Read more at LoveWalter.com. Follow him on Twitter @ LoveWalterHQ

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