29 June 2009

A tale of two dates

By: Jessica B.

Yesterday I mentioned that I went on two dates with guys from Match, and because I’m not a tease, I will deliver on my promise to tell you about it.

But before we get there, two dates in two days with two guys? I know, let’s say it, “holla playa! Heyyyyyyyy. Big pimpin. Oh yeahhhhhh.”
Okay, moving on, I went out with JohnBoy for the first time and Dayton for a second time. Check out my mention of my first date with Dayton here. And if you follow me on Twitter, you’ll know that Dayton has been sending some odd signals lately by saying, “yes I want to get together with you, but I need to keep my schedule flexible so I can go sailing if I want to.” Not the best thing to share, but whatevs, we still got together to see if there is a spark.
Now, let’s dish about the dates.
Date #1: JohnBoy, we’ll always have tacos
I won’t lie, I was really looking forward to meeting JohnBoy. We’ve e-mailed and chatted on the phone a few times, and he was always really sweet and funny. Raised in Atlanta and now living in Chicago, I smelled “southern gentleman” on him (and not Drakkar Noir) and said, yes, let’s meet up.
So we did at De Cero in the West Loop post-20sb wine tasting and I won’t lie, I was really nervous. So much so that my hands were actually shaking a little bit. Eeek that never happens!
Dinner was very nice, handmade tacos and a delish margarita, and JohnBoy was every bit the gentleman I thought he might be. From opening doors (car and restaurant) to letting me order first, to helping me with my chair, it was really nice. AND he even held the umbrella for me when it started raining after dinner.
OMFG who does that?
The conversation was good, few awkward pauses and I think we were on the same page with what we wanted long-term and how we feel about our careers. No, I didn’t say I wanted to marry him and have his babies, but the topics came up very loosely. The date ended well and I told him flat out that I wanted to see him again. Let’s hope I do! And he even sent me a playful e-mail on Sunday morning, and I couldn’t help but smile when I saw it. Oh boy.
Date #2: Dayton – you had me at Rigatoni

I met Dayton Sunday night at Tarantino’s at the recommendation of a work friend, who has very good taste in food. And she didn’t let me down, the Lincoln Park restaurant was a perfect setting for a nice dinner outside and the meal was beyond fabulous. The leftovers will be too.
The locale and food was amazing. The Dayton’s company was okay, but something seemed a little….off and platonic.
First, I was running late, due to Pride Parade cleanup, so I was already in a flushed rush to get there in a decent amount of time because I hate being late to places.
He beat me there and surprised me by wearing….the exact same dirty polo shirt and jeans that he wore on our first date. *crickets chirping* I’m sure this wasn’t intentional but definitely caught my attention, especially when I’m in a cute sundress and accessories. He said I looked “professional,” yet I would have settled for “nice.”
Conversation was a little rough, every 10-15 minutes, he went on “screensaver” mode and would look off into space, making me fear he might pass out at any second. I failed CPR, so don’t look to me to save you on that one.
But we did talk more about work and our personal interests. He made sure to make fun of my sunburn and talk a lot about his dog. A lot. No seriously, a lot. It also came up in conversation that he has issues with his family dynamic, coming from a divorced home. Been there, done that myself. There were definitely awkward parts in conversation and I was the more upbeat of the two of us, maybe it was a bad day?
So the date ended okay with him, with a chaste hug and saying he’d write me in a few days since we weren’t hanging out until next week due to July 4th.
I won’t rule things out with him, but the friend vibe is stronger than ever. So I think I’ll give it one more shot with him and then maybe have the “talk” about how we’re feeling toward one another.
And there are the tales of my two dates.
What was the best/worst date you’ve ever been on?

33 Comments

  1. Maki says:

    Sorry it's day late to read this post, but ahem.. I think I like JohnBoy A LOT. And I think he sounds A LOT better than Dayton. You can't wear the same clothes twice on the date, especially back to back. Do you remember one of Jerry Seinfeld's episodes where this girl wearing the same outfit over and over again? He makes me nervous… :)

    I'm sooooo excited for you!!!

  2. Maggie says:

    forget Dayton! who wears the same clothes again on a second date!? and the "professional" comment? that's just awkward.

    I'm rooting for JohnBoy!

  3. Hillary Deck says:

    I hope you see John again! He seems very cool!

  4. Katelin says:

    oh yay for date number one that sounds like it might have some potential. fingers crossed!

  5. Jess says:

    I'm over Dayton. I like JohnBoy!

    The best date I ever went on was probably my first one with Torsten. We met up for lunch. And then had dinner too, because we stayed for so long. It was awesome.

  6. Abra says:

    I vote for JohnBoy ;)

    My favorite dates are those that play out as follows: date tells me what time he will be picking me up (ex, 7pm) and what i should be wearing (ex, no jeans, but not super fancy). He takes me to a new/exciting/delicious restaurant. We do something spontaneous afterwards.

    Some of my best dates didn't follow that pattern… but that's what I think of when I think "date."

    My worst dates? The ones that I didn't realize were intended to be dates (I'm invited to a movie, I think it's a friend/group thing, turns out to be just the one guy and awkward conversation ensues for the entire night).

    Actually, and I know this comment is getting long but, I think my favorite less traditional "dates" are "day dates," in which I spend an entire day with the guy and we do fun, interesting thing one after the other. Those are really fun, and REALLY special to me (being able to spend an entire day with one person without getting irritated? Amazing).

  7. erin says:

    "screensaver mode". Hee hee!! My fingers are crossed for Johnboy.

  8. Wonderful says:

    Sounds like date #1 was better. My best dates are ones where they last for hours because we don't want to go home just yet.

  9. Ali says:

    Well the good thing is that this is a no-brainer! I think you know who you like out of these 2, haha.

    Worst date I've ever been on? Oy. I went out with a guy I met in class (in college), we went to get yogurt and (get this) he tucked his napkin into his shirt. Sorry…can't do it.

    Now? He's married to a born again Christian type girl. Yep.

  10. SoMi's Nilsa says:

    A) I hope JohnBoy calls and you get to see him again. Sounds very promising.

    B) I can't believe you're giving Dayton another chance. And "talk about our feelings." Based on what you've written about him, he wouldn't know a feeling if it hit him square in the jaw. I say, give him a taste of his own medicine and be unavailable due to the need to keep your schedule flexible should you decide you want to wash your hair and do your nails. =)

  11. Daisy says:

    My worst date= being taken to a Poetry club by this Austrian guy in London and him reading a poem about me on the open-mic.

    Your date with John-Boy however sounds like a winner – can't wait to hear how this one turns out!

  12. Kate says:

    I went out with a Tanzanian guy a few times. He told me he wanted to take me home for Thanksgiving to meet his family and did a couple other creepy things. I stopped seeing him and answering his calls — and he would literally call 10 to 12 times a day and leave messages. I was lucky he never showed up at my building since he knew where I lived.

    Also, my now-husband could be a terrible date. He, like Dayton, also wanted to stay "flexible" — even today he hates being obligated by anything. Once, when we were first dating, he told me we could hang out the following weekend if he "didn't have anything better to do." I still remind him of that very romantic statement. :)

  13. Rebekah says:

    JohnBoy sounds promising! And now I am seriously hungry for a taco.

  14. wekeepsaying says:

    i'm rootin' for johnboy (like this is a competition, CAUSE IT IS!) because of one reason i can't say, and because he totally holds the umbrella for me. always. WHILE putting his other arm around my waist. every time.

    stay with the umbrella man, dayton sounds way awkward…(same outfit? seriously? does he not notice what he puts on?)

  15. nory says:

    If I had to choose a "Team" I'd be all for Team JohnBoy.

    The worst date I've ever been on? I don't think there is enough space in your lovely comment wall for me to leave such details. Suffice to say I've had some terrible ones. Really. Terrible.

  16. Ray says:

    JohnBoy seems promising…can't wait to hear more about him. and De Cero is fabulous!

  17. Kyla Roma says:

    Oh wow! JohnBoy sounds exciting! I hope you can meet up again = )

  18. Yeah, I'm with everyone else (and I'm pretty sure YOU!) when I'm saying my vote goes for JohnBoy. I mean, who doesn't like a southern gentleman. I always wished for that for myself…Instead I married a Mama's Boy straight out of the burbs of Chicago. I will live vicariously through you. Do not disappoint. Please. :-)

    Despite the fact that I'm married, I wouldn't say that I've actually been on a lot of dates. I mean, Hubby and I go out occasionally, and in our very long stretch of dating before marriage, we went out a lot, but I never really considered those dates.

    That being said, the worst one was with a guy that I'd met on the internet (not my Hubby). He'd just moved to the small town that I grew up in. He seemed nice enough through emails, but didn't have any pics, which might have been a flag of some sort. We decided that we'd go bowling in the next town over. We decided to meet there, even though he lived like two blocks away. I arrived and he was already there – I wanted to leave before I even said hello. What a horrible thing to say – but I was so completely unattracted to him. But he'd been very nice through emails, like I said, so I walked up and introduced myself. We started to bowl and LORD HELP ME, it was the LONGEST ten frames EVER. He was not keeping up his end of the convo, at all. I'd ask a question, get a one word response and that was that. I really thought I was going to fall asleep from boredom. After what seemed like an eternity, we finished bowling and I told him I had to get back home. I think I ended up going out to dinner with a friend instead.

  19. fritz says:

    YaY for contestant number 1! my best date was with my fiance (who i met on match) where we went to a haunted house, had coffee, talked for hours then caught the late viewing of Flags of Our Fathers (i am a total history nerd!) good luck!!

  20. lollygagger says:

    Ooh! I hope you get to go out with JohnBoy again – sounds so nice and fun!

    I'm in the middle of setting up one for this week and kinda wishing he'd pick a place and tell me where to be rather than this back and forth…oy.

    One of my worst dates is when the guy made me take the bus rather than get a cab. Yes. The bus.

  21. Ashley says:

    Dating is awkward, I can say that much. My most awkward date was with a guy I met at the bar on my 20th (at least I think it was my 20th) birthday. I went on a date with him the next day only to find myself greatly disappointed. He wasn't as good looking as a remember (alcohol really does skew your judgement) and his life style was nothing near what I was looking for. He was certainly kind to himself in the way he presented the "I work part time in my friends bar and other than that I'm a big loser."

    It seems that Dayton doesn't mind letting things fade out between the two of you if it lets him go sailing so I say let him sail away. If he's not putting an effort towards the relationship this early in he won't later on either.

    JohnBoy sounds like a real winner at this point. If he's even willing to discuss long term with you at this point in the game he's probably looking for something serious. I hope things work out well.

  22. Blaez says:

    Keep Johnie and ditch Dayton. seriously, the same dirty clothes? ewe…

  23. Angela says:

    I think, since you don't have any feelings invested towards Dayton, that you could PROBABLY let things fizzle out. Unless there's a REALLY strong friend vibe, if it were ME, I probably wouldn't go out with him again.

    But JohnBoy sounds like a winner so far!!! Definitely keep us in the loop! =)

  24. Hal says:

    I vote JohnBoy! And Tarantino's is soooo good, I live right near there and it tempts me every time I walk home.

    Glad to hear the dates went well, i'm so glad! It was awesome to hang out this weekend!

  25. Andhari says:

    Oh girlie, you're a way more nicer girl than me. I woudln't even give guys like Dayton another chance or another date. Lol. Would have made excuses to leave as soon as I sense the conversation gets boring. Johnboy in the other hand, sounds good. Can't wait til you go out with him again.

  26. ChicagoSane says:

    Who opens doors for women (every door) and holds their umbrellas? EVERY MAN.

    If a male does not, he is a boy. Yes even gorgeous to-die-for men do this. It's because momma raised them well, not because they're overdoing it.

    If a guy does not open the door for you, HIT THE FUCKING ROAD.

    And wearing the SAME clothes on 2 dates? GROSS GROSS GROSS. Boy needs a mama to clean his shit, not a girlfriend.

    Congrats, nonetheless!

  27. Auburn Kat says:

    JohnBoy definitely does sound promising!

    You had quite the busy wknd!!

  28. LBluca77 says:

    JohnBoy sounds great. I don't think I have ever gone on a date with a guy that wore the same outfit on the first and second date. Don't boys understand we notice those things.

  29. JonBoy #1 sounds waaaay better… but I think it´s cool that you went out with both of them, that way you can have a better perspective of what you like and what you dont like.

  30. Hmmm, Dayton sounds a bit odd. Who says a woman's dress looks "professional" whilst on a date! And…since when is a sundress professional anyway?

    I, too, am rooting for JohnBoy! Good for you for giving people a fair shake by going out multiple times before making decisions. I used to be a one and done girl myself and probably let some great guys go because I rushed to judgment.

  31. Erin says:

    Ohhhh, I like that JohnBoy! I can't wait to hear more about him! :)

  32. Mandy says:

    I am excited to hear more about JohnBoy! He sounds promising. =)

  33. Jersey says:

    Ooooo I'm rooting for JohnBoy. You can tell just by the way you write that you like him. Plus, I have a theory- the ones we like more we write less about- kind of to keep all the good details to ourselves in a sense. Just a theory though…

    Good luck!

 

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