30 June 2009

The awkward part of the date

By: Jessica B.
So now that I’ve told you about my weekend dates, I need to share the most awkward part about the date with JohnBoy, which was the end.
For me, the end of dates is the most uncomfortable. Not the uncomfortable pauses in conversation during dinner or after I realize this guy isn’t going to work out, it’s the end, after the conversation is over, dinner is paid and it’s time to say goodnight.
There is always that moment when it comes time to say goodbye of…now what? Do I hug, do I kiss, what is appropriate?
I don’t give up or do anything I don’t want to, but I never know if I should lead or initiate something. For someone (aka me) who is rather aggressive when she wants things, I get very timid and “traditional” when it comes to dating.
Back on point, when JohnBoy drove me home after our date, there was definitely an awkward moment of…what happens now? Outside of me getting out of the car and going home.
So we’re sitting in his car, talking, I’m exhausted and ready to pop out one of my contacts ASAP and we’re just…staring at each other.
Finally after crickets started chirping, I said thank you for the millionth time (I meant it too), I didn’t think he was going to do anything (other than say thank you) so I go in for a hug. Not totally awkward, but the car isn’t the best place for a proper one, and then…..oh what the h*ll, I planted a slightly drunken kiss on his cheek and got one in return. I mean, he did pay for dinner and acted like a total gentleman all night.
This may be sad to admit, but it’s been a while since I had a nice kiss from a guy and if I had one or two more drinks, I would have definitely have “nicely” pushed him against the car door and gone in for some tongue action, but I didn’t.
And after his “surprise” half-kiss, I hopped out of the car. I know, I wish I would have lingered a little bit too. I don’t want to “peak” too early in hopefully our string of upcoming dates.
What part of the date do you usually fine the most awkward, or what do you do at the end of the date to avoid the awkwardness of saying goodbye?
Note: Thank you for the great comments on the date post yesterday :) I so appreciate all the kind words. And after reading everyone’s comments, I agree, I think it’s time to vote Dayton off of “Match Island.” I just can’t get over that wearing the same shirt thing either! You guys give great dating advice ;)


  1. ChicagoSane says:

    I have a very strong rule about first date "ends" that I have never broken once.

    If she shows me interest, I kiss her.

    If a woman doesn't show me interest, I bail. I'll be her friend, but rarely will I _ever_ make a move after a first date. In fact, I can't think of one gal I've ever kissed where it hasn't been on a first date (because she showed interest), except for women who have been my friends who have kissed me later in our friendship.

    Signs of interest:
    1. Touching me. This is key. If she's not doing the casual arm grab, hand touch, shoulder grab, whatever? No kiss. EVER.

    2. Looking at my lips. If #1 doesn't happen, I _might_ consider her interested with this, but it's a rare one that takes it.

    That's all. A woman who isn't interested in me enough will show it by NOT being physical during the date.

    I've heard it about 5,000,000 times though from gals I've dated once: "Why didn't you kiss me?" Because you're a little girl who has no idea how to woo ME. It's not about me wooing YOU, I'm a man, I'm confident, I don't have to play your bullshit games. Woo ME and you'll get a kiss. Don't, and I will go out on a first date next week with someone else who IS feminine enough to understand the game starts with you showing interest.

  2. Auburn Kat says:

    I am with you…the ending of a date is always weird! Does he like me? Does he not like me? What if he tries to kiss me and I don't want to kiss him? What if I want to kiss him and he just gives me a hug?

    My solution, give him a hug before the moment becomes weird!

    Then again, I haven't been on a date since I was…crap I don't even want to think how long it's been….

  3. gah! i don't even know what'd i do in that situation. i haven't ever been put in it, i'd probably just run the other way.

    but seriously jess im loving your dating stories. i'll continue to live through you for the time being.

  4. P says:

    I'm generally better at the awkward part of the date than the conversation bit. On my first date with the guy I've currently been seeing, we were sitting on either side of a booth, and when he came back from the toilet towards the end of the night, I instructed him (rather drunkenly) to come and sit next to me instead. Then midway through him talking I lunged. Turned out for the best as he said he had been still trying to work up the nerve to kiss me, so I had helped out with that!

    That being said, I have a male friend who started seeing a girl a little before I started seeing this guy, and he said he never kissed her until their third date and it was only because she YELLED at him about it??? Huh???

  5. Katelin says:

    aw that is cute. but i totally agree, the goodnights were always the most awkward part of the night, i usually went for the hug, haha.

  6. Awww, that's cute, even if you think the end was a bit awkward. Keep him wanting more :)

    Best dating advice I ever got was from my mom and she said "Let him chase you until you catch him"…. hahaha….


  7. erin says:

    The end of the date is the worst! I usually launch myself at them for an awkward hug and then I run away. I have to say, I really love it when the guy confidently moves in for the kiss. (Unless I don't want to kiss them, of course. But if I do? Yowza.)

  8. Miss Grace says:

    I definitely find the goodbye portion to be the most awkward.

  9. Jersey says:

    Yay! I just saw on Twitter that you have a new date set up with JohnBoy! Work it, girl!

    (not to Twitter Stalk you or anything, lol)

  10. I agree, the end is always the worst. Either someone has to make the first move, or you both awkwardly step around the issue. If it's a really amazing date, things flow nicely, but in most cases it gets pretty awkward. I

  11. Cheryl says:

    Cars definitely make things more tricky. I went with a thank you and usually let a guy take it from there. Talk about traditional!

  12. Jaime says:

    I've never been on a date with someone I wasn't friends with before hand, so it's never been awkward for me. I'm lucky like that. But at the same time, I've never been on a REAL date – where we go out to dinner at a nice place or something. Not yet, anyway.

  13. the thought of the end of dates make me cringe (even though it's been quite A LONG TIME since I was last on one)

    the silence! the awkwardness! aah!

    but you handled yourself and the situation quite nicely!

  14. Jersey says:

    The end is definitely the most awkward. But a close runner-up is the meeting, I think. I mean, if this is a blind date or an online set up date. You never know if the person really looks the way you think they will or if they are going to take you and chop off your head with an axe.

    Vivid imagination. Sorry.

    But until the nerves calm down, that's a close second for me.

    Let us know when you set up another date! Yay!

  15. The end of a date is so nervous for me too. I remember with my now boyfriend I had to take the initiative to kiss him the first couple of times and it made me wonder whether he was actually into me at all. He later explained he wanted to be a gentleman by not forcing anything on me and he wasn't sure whether I would appreciate the kissing. So who knows, maybe he really like the kiss you gave him and just wants to be a gentleman?

  16. SoMi's Nilsa says:

    So, I think it's kind of cute when there's this awkwardness at the end of the date, as in, both people are interested in one another and don't know what to do next. Way better than the awkwardness that comes when one person isn't interested and the other person is lingering too long. ha.

  17. lollygagger says:

    That's cute! I like it. For me the end is the most awkward definitely b/c I either want to book it or want the guy to make a move. Ah! Now I'm freaking because I have a first date tomorrow. Ok. Will calm down. Yay for you!

  18. Angela says:

    Awww, cute!!! I don't think you burned any bridges with JohnBoy just over an awkward end-of-night kiss.

    I definitely think the end of a date is awkwards, too, especially with a new guy. You don't want to kiss him too early and let him get the wrong impression, but you don't want to NOT kiss him and have him think you're uninterested.

    I will always let the man initiate the first move. When I'm sober, that is. When I'm drunk, that's another story, like you said. I'm all about pushing up against walls in that case.

  19. I am impressed at how confident you are to even put yourself out there.

    Weighing in late but yes – any guy who wears the same sloppy shirt on 2 dates in a row is a no go.

  20. Jen says:

    I think you did the right thing, and it's totally cute and a great setup for the next date. :-)

    As for this Dayton fellow, psht. If you're just not feeling it (and I agree with the others) vote that sucker off! Don't waste your valuable time with someone who isn't giving you a good gut feeling. You're worth more than that!

  21. Maki says:

    Well, I must say, your move was perfect for a perfect date!!! It seems JohnBoy is genuinely a nice guy and gentleman. You can always attack him when you see him next time…

    Sometimes, taking it slow is a lot better than aiming the bull's eye = mouth… I think you're the cutest girl on the planet and I don't want you to change a bit…

    I had had awkwardness in my past dates only when I wasn't into the guy because I was afraid that he's going to kiss me which is totally opposite case from your date w/ JohnBoy. Your awkwardness comes simply from you liking JohnBoy, hense the nervousness. Charming ;)

  22. Jenn says:

    i've been dating/engaged to/married to my husband for so long that i forgot how totally awkward that moment is when you first start seeing someone. it's usually best resolved through a lot of alcohol during the date (at least in my college years it was – haha). you are too funny! :)

  23. Blaez says:

    i think for me it has to be the beginning and the end…

  24. Andhari says:

    I seriously think what you did is safe, girl. In the end of a date if a guy doesn't make a move with a kiss first, it's like what you should do is a hug and a cheek on the kiss. That's respectable :) let's hope he kisses first in the second date :)

  25. Moonjava says:

    I think you got it right, the end is the worst. I go for the awkward hug (and I was the initiator). I feel that the handshake is kinda weird, and I can't do a kiss on a first date. Still a traditional gal…lol.

  26. I'm also most awkward at the end of the date. In fact, I'm so awkward that I actually try to rush out of the car to avoid the awkward "should we kiss" silence.

    In doing my rush move, I've almost fallen out of the car, and once — when the guy got to me before I could pull it off — we banged heads. Wups!

  27. Hi! I'm Erin says:

    I wish I could give you dating advice, but I've been out of the game for too long. But, I agree with everyone about the same shirt thing. I'd prefer my guy to pay more attention to detail if I had it to do over again.

  28. Mandy says:

    The end is always the worst. I think that you handled it well. He was probably sitting there trying to figure out what to do as well.

  29. Jess says:

    I think either the very end, like you described, or the part where it seems like you should wrap up whatever it is you're doing, but you're not sure if the other person is ready, and you don't want to be rude, or cut it short, but you also don't want to overstay your welcome. Not good.

  30. Maggie says:

    the end is sooooo awkward!! my first date with the ex was like neverending because neither of us knew what to do..after 20 awkward minutes I got out of the car and was disappointed.

    good for you for taking the initiative, even if it was just on the cheek.