The Dating Lifeline

2009 December 16
by Grace Boyle

I was 13 and in seventh grade. I had convinced my mom to drop me off a block away from the movie theater where she thought I was just meeting friends for a Sunday matinee, but really, I had been asked out. You know, my first real date. I was meeting a boy.

Truth was, I was so nervous and uncertain about it that I convinced my friend Anna to come along with me (but didn’t tell my date). We arrived before my date (let’s call him Timmy). When Timmy arrived (his dad dropped him off on his motorcycle) he looked at me and smiled. Then he turned to Anna and his eyebrows furrowed. I started to sweat and squeaked,“Err, Anna wanted to see The Sixth Sense, too.” Timmy let out a big sigh.

I bought my ticket with my allowance money. We walked into the movie theater, Anna on my right, Timmy on my left. He bought me buttery popcorn. He asked to hold my hand halfway through the movie. I said, “I guess.” My palms felt clammy.

There was no second date.

The Middleline

Five years later, I’m in college. Newly single and surrounded by thousands of immature 18-year old boys. Seriously, dating is like being in a jungle and you need to be prepared with the right equipment and support team.


Photo Credit

I was sitting in my Modern American Social History class. Front row. I was chewing on my pen and I felt someone staring at me. You know how you can just feel it? I slowly turned and a larger-looking guy with puppy eyes, I hadn’t even noticed before was staring at me, smiling. Naturally, I smiled back. I smile all the time, it wasn’t a big deal. Then I turned away.

Repeat this scenario, for the next five classes. Smiling college boy finally talked to me as I walked out of the class. He asked if I wanted to have dinner sometime.

[Now let me interject. I have this rule. If someone is assertive and asks me out, I will say yes. When single and asked out, I haven’t turned anyone down yet. Simply because, you never know. If anything, maybe it’s a crazy you can retell a story later or you meet a new friend, or a good meal, or a boyfriend. My point is, I’m open.]

I say yes. He picks me up, I live in a suite with three other girlfriends. I’m a sophomore in college. He proceeds to tell me he hasn’t made reservations anywhere and asks where I would like to go.

Uh, great. It’s Friday night, we drive to one restaurant and it’s packed, one hour wait.

We drive to another spot that’s new, I don’t even know what it is. We roll up and get out of his car. It’s a fast food, chain Mexican restaurant (think Chipotle). I’m not picky, I really am not (plus, I love Mexican food) but first impressions mean a lot. He didn’t plan anything either. I’m a good sport and always down, so I got a plastic tray, got into line and ordered my burrito.

He tells me my smile makes his day because no one ever smiles back at him. We talk about life, but I already know it won’t go anywhere beyond a friendship. He drives me home and invites himself upstairs. He then invites himself to the party I’m going to with my girlfriends. Clingy, yes. Sweet, he was. Not for me, most definitely.

That was our only date. I took honesty as the best policy and learned a lesson in why I am upfront.

Too Much, Too Soon

A friend set us up. He had just come back from duty in Iraq. Not an easy scenario, completely understood. I was gentle and kind.

He brought me a dozen roses. Sort of aggressive move for a first date, but sure, thank you, they were beautiful. He knows I’m Italian, he brings me to a delicious Italian place. Thoughtful. Our conversation consisted of questions like, “When you’re driving, do you like to leave the windows up or down?” No joke. I answer, “Um, it depends on the weather? Or my mood…” Crickets.

After dinner, he asks if I want to stop by his house. I didn’t want to and said I was getting tired. He persisted and finally I said, “Okay, sure.” Little do I know, this is his house that he grew up in. His family is waiting to meet me. Yes, this is a first date. He brought me to meet his family. They had presents for me and knew all about me.

I scurried out of that situation right away.

The Lifeline Continues

We all have this dating lifeline. The stories that shape us and the experiences that make us laugh or cry. I think it gives you a backbone. It can be frustrating but the thing is that dating when you’re 13 or 23 is relatively the same. It is still awkward, it doesn’t always work out, we can fall in love, we can break hearts and have our heart broken…and my palms still get clammy.

Yet, I keep dating, I keep talking to people, I’m open and I remember a date that simply seemed friendly and thought wouldn’t be anything more turned into a wonderful long-lasting relationship (oh, um we’re no longer together, but still). For me, it’s quality over quantity and the more you know yourself, the better off you are.

Good luck in the dating jungle. I’m right there with you. When you think you’re the only one who has bad dates or he brings you to meet his entire family, think again.  It’s part of the process.

What’s your dating lifeline or story? Commiserate and share.

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  • Carlos Miceli

    “If someone is assertive and asks me out, I will say yes. When single and asked out, I haven't turned anyone down yet. Simply because, you never know.”

    This is too valuable info. You shouldn't tell guys this.

    Especially not me.

    Pick you up at 8?

  • Emily Jasper

    Grace, thank you for sharing. I know most of us could probably go on for hours over cocktails or coffee about dating, but I love the use of Dating Lifeline. It does go up and down. I've been the first girlfriend for a number of guys, putting me in the dominating position when I really want someone to take the lead; a guy told me he loved me, walked out the door and literally moved to Texas without telling me, only to then email me when he was drunk; I've had a first date show up for lunch hungover with no wallet; I've been left, stranded, cheated on, and had so many unsuccessful first dates I can't even imagine trying anymore. But I do…

  • Grace Boyle

    @Carlos I'm honest and open, what can I say? It's not as though my 'date book' is overflowing right now.

    Oh and, I will be ready at 8.

  • Grace Boyle

    @Emily Thank you for sharing. Whenever I get together with a group of my girlfriends our stories are overflowing with sadness, laughter and confusion. It makes me feel good to speak to others about our experience and remember we're not alone and it's all part of it.

    I commiserate with you…none of those experiences are easy. But someday (maybe even now) we can look back to reflect and laugh.

  • David

    Your 13-year-old dating self was adorable. Gotta love those innocent first date stories. Clammy hands, buttery popcorn, awkward moments, and ASKING to hold someone’s hand. Priceless.

    Fast forward five years to a guy that tells you your smile makes his day because no one ever smiles back at him. The smile making his day is cute. The part about no one ever smiling back at him sounded a bit creepy on his part. I bet you were wishing for Timmy to return. Sounded like Timmy had more game.

    And military man. Oh no, no, no! Too much too soon is right! Sounds like my Lady Gaga date from last week that called me 4x in under 1 hour!

    PS (Do you mind if I link to your blog on my site? I've been enjoying what you write and I figure why not share the goodness with me readers.)

  • Ron Bronson

    I think a lot of it has to do with how our lives evolve, where we think we're headed versus where we are…and how someone fits into that. So it seems like a lot of rapid misfire until you get to a place where things and people make a bit more sense. Easier said than done, but..the experiences are usually worth it in the end. Or so I'm going to keep telling myself. Thanks for sharing.

  • Grace Boyle

    @David That 13-year old date of mine is now a Hollywood film producer. Maybe I should have let him kiss me (on the cheek of course) back then. Shit.

    Yes, smiling college boy was a bit creepy…he didn't have game, so my empathetic self felt bad for him, but you don't want to start feeling bad already on your first date.

    I told you about this military man (not quite my style anyway) after I read your Bad Romance post. This one kills me. His entire family!? Luckily, I was a good sport and kept from either crying or just bursting out in laughter. I humored them…

    Of course you can link to my blog. You're so sweet for asking. I would be honored. Thanks for sharing, commiserating and I'm sure I got a good laugh out of you. My work here is done.

  • Grace Boyle

    @Ron Thanks for sharing, as well. These stories (albeit funny) were also retold because it shows where we've come from and hopefully others can learn from them too. I always say, experience is knowledge and I still believe it.

  • Rebecca

    Hahaha, your first dating story sounds just like mine! Movie, brought the friend along, clammy hands. Further evidence we were separated at birth or something 😉

  • tarable

    Grace, my dating lifeline is too long, intense and inappropriate for a blog comment. (But since you've already heard some of my better stories…you already know that.)

    However, I did want to share the story of a guy that I dated once. He was really sweet but also highly neurotic. (And not in that cute Jewish way.) We were together for probably seven months but things didn't work out. The very next guy I dated after him, I married.

    I ran into that same guy a few months ago and we were catching up. He said that since we had broken up, he had dated three other women who ALL went on to break up with him and marry the very next guys they dated. I told him he should start advertising his services.

    I guess when it comes to dating, we all know where our strengths lay.

  • Rich DeMatteo

    After 3 serious relationships starting freshman year of college and ending a year after I graduated from College, I've been on a 4 year hiatus from the serious dating world.

    There have been many funny, awkward, and straight up weird moments in going on first, second, and third dates. Maybe it was purely my lack of interest in seeing things develop seriously, but not much has lasted longer than a month in 4 years.

    I typically go for quality, but I also go for quantity in quality. Maybe that's confusing, but as the years go on I find I change even more. What I want in a girl changes rapidly, so why settle till I know?

    Your thoughts on this were awesome, and hopefully “Smiley” learned how to plan a date for his next smile victim.

  • David

    Well I have a confession. I didn’t want to say this earlier because I was too embarrassed to admit it, especially following my Bad Romance post, but I can honestly say I feel your pain and can relate 100%. What am I talking about? Well…

    When I was 19 (freshman in college), I asked this girl out. During the date she asked if it was ok if we went back to her parents house afterwards just for a bit because they were throwing her a party. I looked at her as if to say “What the hell are you talking about, a party?” It turns out it was her birthday and her entire family was waiting to meet me at this big birthday party of hers! Talk about awkward! And it gets worse!

    Not only did I feel like a jackass not knowing it was her birthday (would have at least got her a card), but now I had to meet 25+ of her relatives all at once when I didn’t even know her! Now the worst, WORST part – her Grandpap was drunk and kissed me within 5 minutes of walking in the door. I hadn't even kissed her yet, but had involuntarily madeout with her Grandpap!

    I think I just broke out into a cold sweet reliving that horror. Anyway, the point is no matter how bad you think your dating life is, I probably have a story that will make you feel better about it all.

  • Grace Boyle

    @David Oh, I've never met anyone else with the family on a first date scenario. I experienced some anxiety in hearing your story. Don't be embarrassed, you rolled with the punches. Even got a little action from Grandpa (kidding). Sorry, had to.

    I'm happy to hear that whenever I'm feeling bad about my dating stories I will promptly contact you and ask for a scenario that can top mine.

  • Grace Boyle

    @Rebecca Ha, everyday something new. It really seems like we WERE separated at birth 😉

  • Grace Boyle

    @Tarable His self esteem really must be shooting through the roof.

  • Grace Boyle

    @Rich A hiatus is good. It's cleansing, refreshing and a time to be healthily selfish.

    Quantity in quality (if possible) is ideal. Sometimes it's out of our control, sometimes not. I wonder how Smiley is doing…I can just see him now, dopey smile, staring me down. Sweet.

    Glad I could keep you hooked on this post 😉

  • Kat_ksk

    I haven't had too many awful first date stories, but I have been asked out in some pretty weird ways.
    The first time I was asked out for real (not a kids at school thing) was in the ocean, like actually in the water, by a cute mexican mormon guy (weird combination). Once I was asked out in the subway in the middle of the night, and it wasn't even a crazy homeless person, he was probably otherwise very nice and… normal.
    Then there is this guy who I met a long time ago but never went out with, and he just asked me out for new years…. I mean isn't that weird for a first date? That's the one night of the year when you can't really sneak out early on a really bad date.

  • Grace Boyle

    @Kat_ksk Ha, that is funny. I never talked about the way people asked people out, but that can be equally as funny. Thanks for sharing :)

  • Elisa Doucette

    I adhere to the same rule of dating that you do. If anyone asks, I will say yes. What does it hurt, right? You never know who you may just kind of like or have never looked at that would be a great person to date. The downside of that involves the fact that the last time I was asked out the OC was still in regular syndication.

    I have many different stories in my dating lifeline. Well, maybe not MANY (makes me sound like I get around far more than I do.) Best one was the guy I first dated when I moved back to Southern Maine. We went out quite a few times, and the last time we were sitting on a bench in a park when he flipped out. Like FLIPPED out. Jumped up, said it was too late and cold and damp outside. We went back to his apartment where he promptly kissed me good night and went inside. Next day he called to apologize for being so weird the night before. See, he was getting bitten by moquitos the night before and was afraid he would get West Nile Virus if we didn't leave. But he went back to his apartment and called his Mom and she calmed him down.

    Needless to say we didn't go out ever again after that. :)

  • Grace Boyle

    @Elisa You went on the date with supermarket man though, right?

    Back to the topic (hehe) that's indeed a unique story about West Nile Virus man. These stories really do shape us, I keep seeing it and I know it's true. Even if they are embarrassing, tragic or sad…

    Also, to the point of saying “yes” to go on a date I really keep my mind open like a parachute. A lot of people tried to come up with scenarios where I would have to say no and honestly, all dates don't have to have the same expectation. So it is good to say yes…we never do know. Thanks for sharing :)

  • Elisa Doucette

    Ooops, you're right. The supermarket guy totally did ask me out. Just this past summer. Then never talked to me again after our second date. Timeline or not, dating sucks!

  • Mehnaz

    Fab Post Grace!

    I too, love the fact that you're open to being asked out. And it really can't hurt. Unless he's a creepy weirdo, but that's if you don't trust your instincts :) I'm really picky, which is probably something I need to get over at some point. But I agree that first impressions are probably important here.
    Thanks for sharing this with us.

  • Grace Boyle

    @Mehnaz I am picky as well (in the long run) but going on a date, can be so harmless. I thought I would share some personal stores to make everyone laugh but also because I was assured almost everyone had a story to tell.

    Also, I don't think you should stop being picky. Maybe being picky, but open is a good combination. Don't step down from what you believe in or want but also know that sometimes the first time you meet isn't indicative of your future or the relationship with that person.

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  • Jim

    Great idea for a post, Grace. Refreshing to hear that there are women out there who will accept a date with someone “unconventional” on the chance that they might hit it off. Also sounds like there are quite a few clueless guys out there in need of dating advice. New blog niche? Best of luck in your future dating lifeline!

  • doniree

    I think you nailed it with that part at the end about the more you know yourself, the better off you are. I mean, we'll see where that takes me now, but I feel like I have a better grip on myself this year than I ever have before. I was stubborn about starting a relationship with a guy who was and is so ready to jump right on board my crazy train. Can't resist someone who thinks your version of crazy is adorable, right?

  • Grace Boyle

    @Doni I know, resisting doesn't work. When it naturally occurs we got to toss out the timing and practicality and just realize this might be the next best thing. I can't wait to hear how it all unfolds 😉

  • Grace Boyle

    @Jim It's refreshing for me as well because it means I am open to change and new opportunities. And yes, you're right by me being pretty open to any date/person I am subject to many clueless guys in the dating world. It makes for a good blog post, right? Thank you :)

  • Grace Boyle

    @Doni I know, resisting doesn't work. When it naturally occurs we got to toss out the timing and practicality and just realize this might be the next best thing. I can't wait to hear how it all unfolds 😉

  • Grace Boyle

    @Jim It's refreshing for me as well because it means I am open to change and new opportunities. And yes, you're right by me being pretty open to any date/person I am subject to many clueless guys in the dating world. It makes for a good blog post, right? Thank you :)

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  • cusoon

    Landed on your blog through random web surfing. Excellent blog. I agree with the quality over the quantity part as well as the if asked then will accept since we never know when we will meet Mr/Ms. Right. First date disasters for me include being asked if I wanted to have kids on my first date. I was drinking coffee when he asked me @ kids and I almost fell off the chair.

  • Grace Boyle

    @Cusoon Thank you. I'm happy the Internets lead you here. Wow, that's pretty scary about being asked about having kids on a first date. I would spit out my food!

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  • Mike

    I don't have a lot of funny dating stories, but I did once date a girl who stabbed a cockroach with a fork when it crawled across the table. Not a “oh my god a bug I'm gonna squish it” stab, but a “I kill people for a living” kind of stab. Then she wiped the fork and kept on eating with it.

    We never got anywhere, but I'd like to imagine that these days, she's in a happy relationship with some lucky guy, occasionally threatening him with sharp silverware whenever they have a fight.

  • Grace Boyle

    @Mike Haha, I just laughed out loud. My question is, WHERE were you that there were cockroaches at the dinner table!?

  • john

    Very good write up. very funny story. I would like to wish you all the best in

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