Funny things start to happen once you’ve been on the dating sites for a while. You start to get the “out-of-town gentleman caller.” These are guys who say they will “conveniently be in town for business” on such and such a date and wonder if you’d like to get together. At first this sounded like the perfect scenario to me. They were here for a couple days, we’d have a dinner, maybe more, and they go away and never come back. Or, they are married.
The first gentleman caller was going to be in town around the time of the Boston Marathon (which I was running). I told him as such and that I might not be much fun and certainly wouldn’t be very mobile but he said no worries. Well, the date was to be on a Wednesday and as soon as I woke up on Tuesday after the MONDAY marathon I knew I was in no shape to do anything. I messaged him in kind. His response? “Figures.” My response: “dude, really? I just ran a bunch of miles and my legs are killing me.” His retort? “Predictable.” So the next time a man from out of town came along, I was wary. But I figured I’d give it another try.
The first question I asked Cinderella (my name for him, this will become clear in a minute) was “are you married?” His answer was no. I’m pretty sure I brought it up a few more times until I was convinced. He seemed normal enough after our chat so I agreed to a date – a month in advance. He was a planner this one. Maybe this is crazy? I felt I was being proactive, filling up the ol’ calendar, making shit happen in my dating world. We texted and messaged a few times, we even talked on the phone. He seemed like an honest to goodness normal person.
The day of the date arrived – the plan was dinner and a Red Sox game. I had gotten the tickets myself so I wouldn’t feel beholden to him: always be mindful of the money put out vs. what you’re supposed to put out ratio. He arrived to dinner before me and at first site I knew there would be no putting out that night. However, I was going to give this date 100 percent – I would listen, I would talk a bit about myself and see what worked. So I listened to him tell me about his TWO failed marriages and the myriad reasons for their failures. He brought up church and the Big J a lot, which for some reason made my use of the f-word increase exponentially. I didn’t do it on purpose, if you have faith, I support it, but I just couldn’t stop it. It was beyond me.
Next stop, Fenway. Before we go any further it’s important that I tell you I told him before the date began that I get up at 3 a.m. and I would be leaving so as to get home by 9. Period. These are my rules on school nights. Like it or lump it and he agreed. It was an incredible night to be at Fenway, it was the 10th anniversary of the World Series win. I was like a kid at well, a ballgame, and so we didn’t chat much during the festivities. The game started, we got beers, and I started staring at the clock waiting for the witching hour at which I’d turn into a pumpkin.
At 8:30 sharp I said I had to leave. I encouraged him to stay, to enjoy the game, to be sure to have a Fenway Frank. He walked me to the Yawkey Way exit, gave me a hug and asked me if I’d ever come to Maryland. Ugh. Yes, you read that right. I left him at Fenway.
A week after the date, I received a hand-written thank you card. It was awkward and strange and just a little weird. He also said he’d be sending me a gift. A month later I received a box from Amazon including… wait for it… Ray Donovan Season 1 on DVD. Such a romantic guy! Needless to say, I haven’t talked to him since.
Looking forward to sharing my stories and getting your advice…K
My first foray into online dating was a boy I call Nemo. We met on Plenty of Fish, get it? Anyway… I change the names to protect the nice people who deign to go out with me.
Nemo had a great opening message to me. Most people were saying “hi” or “hello” or “what’s up” or my personal favorite “Hello my Queen”. Nemo actually spoke TO me. He said:
• A. You look familiar
• B. Why were you walking down that street in your pictures?
The picture he refers to is one of my profile pics of me walking down 5th St in Southie. Right in front of his childhood home.
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A high school friend was driving me to the airport at the end of my recent visit with her. After having just seen one of THE all time movie tearjerkers ever made, The Fault in Our Stars, she said she was going to have to have a conversation with her daughter about the fact that there “are no Augustus Waters in this world.” For those of you who have missed this literary tome, Augustus Waters is the boy in the story who falls in love with the girl and is romantic beyond that of men of his age. Or any age for that matter. For me, it was Lloyd Dobbler holding a boom box in the rain. We all have that guy – that Prince Charming like character that we have looked for (and maybe found) our whole life. My friend thinks this is wrong and that this kind of expectation will set up her daughter to fail, or to be alone, or to be constantly disappointed. I understand her thought, but I couldn’t disagree more. Why can’t we aim for Augustus, Lloyd, Romeo… whomever?
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Yep, it’s true. After breaking up with my boo 9 mos ago, I’ve decided to jump back into the dating pool. And by jump I mean poke a very cautious toe into the most passive form of dating – the online kind. I tried eHarmony once while on vacation, after the breakup and two bottles of wine. It was a “free weekend” so I thought why not! After an hour of answering inane questions and one more glass of wine, I got this…
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Kennedy is a smarty pants. Every morning she shows off her knowledge of all things pop culture during “Can’t Beat Kennedy,” everyone’s favorite part of the “Karson and Kennedy” show on Mix 104.1. When she’s not on air she’s hanging out at the L Street Tavern, sneaking her dog Elvis onto M Street Beach for a game of catch, or checking out the incredible music scene in Boston. Newly single, she’s dived into the world of online dating and has determined she is very bad at it, but knows it’s funny to watch. She loves a good adventure, fears nothing but tinfoil, and wants to try everything once. And the fun stuff twice. “And I’m serious about the tin foil,” she says.
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EDITOR AT LARGE
CHIEF FASHION CORRESPONDENT
Anna Paula Goncalves
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