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Ask Jono: Date Goes Badly, Everyone Becomes Confused

Ask Jono: Date Goes Badly, Everyone Becomes Confused

By Jon_Skindzier

Dear Jono,

So I've been majorly crushing on this guy for about a year now. For the most part, I'm pretty bubbly and outgoing, but I haven't had much experience with boys. Therefore, whenever a cute one comes within my range, I tend to jump into the nearest supply closet and hyperventilate until he goes away.

For the first couple months after I met him, we were in a class together and I would always catch him looking and smiling at me. ALWAYS. I'm talking at least every other day, always. We worked on a project together in the same group, and we shared a few short conversations in which I found out some basic stuff about him. But then the school year ended, and I assumed we would just go our separate ways and I wasted too much time.

That is, until we started school in August and I had three classes with him, plus two after school activities.

I took this as a sign that maybe the heavens think we are destined to be together. Since he's kind of shy, I figured I would try making the first move. So after many months of working up the nerve, I put on my big girl pants and asked him out on a date, and he actually said yes!

Only the date went really awful and was possibly the most embarrassing thing I've ever experienced. (Let's just say there was a soda spilling incident.) I ended up looking completely idiotic, and I figured he would never want to hang out with me again. I cried like that entire weekend. Then, on Sunday night, just as I was preparing to go back to school only to be constantly flung into situations where I would be taunted by my one true love, he called me and apologized that the date went so badly. I was so happy, I had to restrain myself from screaming into the phone. So I figured he still liked me, and that I would just let him ask ME out on the next date this time, right?

Except that never happened. We never actually talked about the date again. I just assumed that if he was into me, he would have asked me out by now. For the most part, things are kind of awkward and we never really converse anymore. However, I still catch him looking at me. Is it one of those cases where he was waiting for me to ask him out and I was waiting for him? Do I wait for him or should I just go for it? Does he still like me, or have I missed my window of opportunity? If I have, is there a way I can make this whole situation less awkward, considering I have to spend most of my time at school near him?

Thanks a lot,
A Very Awkward Soda Spilling Girl

I AM SO GLAD THIS HAPPENED TO YOU. Well, no, of course I'm not; I feel bad for you. But I've used this exact kind of date disaster as an example on more than one occasion, and it's nice to know that I'm not the only one who's ruined a date because my limbs couldn't differentiate between "pick up that coffee" and "punch that coffee directly at your date as hard as you can." What sucks about clumsiness (or any other embarrassing date failure) is how unfair it is; everything can be going perfectly, and then you drop one carrot cake on your date's head, and bam, a good date becomes a terrible date. Every charming thing you said is completely negated forever and nobody will ever love you.

That's how it feels to you, anyway. Luckily, the dude is probably less fixated on that one terrible disaster than you are. So I guess the first issue is: how was the rest of your date? Were you guys making any sort of connection, or was it pretty awkward the whole time, or did you just walk into the room and immediately dump Pepsi on his face? Furthermore, what happened after he called and apologized? Did you say "Okay, that was awful, but we should try again!" Or was it more like: you said "Okay," and then he went "Um," and then you went "Er," and someone coughed, and then you both awkwardly hung up. The guy's behavior since then could mean two different things, and you have to help me fill in the blanks here.

Here's my best guess: he constantly stared and smiled because he did in fact like you, but he was too much of a hopeless goon to ever actually approach you (and he still is). You assaulted him with a beverage, and he felt bad enough on your behalf that he called you to take some of the blame (unless he was super-awkward during the date, in which case this was a legit apology). Either way, he was calling to gauge how you felt about him. Think about it: if a date is irredeemably horrible, you don't call the other person to reminisce about how awful it was; you just crawl into bed and wait to die, or for it to be Monday. You only call if you want to salvage something from the mess. I guess it's possible that he's just very gentlemanly and felt bad about the whole thing, but in that case, I don't think you'd catch him staring goonily at you from across the room. The phone call plus the staring (assuming it's the meaningful kind of staring) makes me think he just doesn't know how to proceed.

If I'm right, then all this guy needs is a clear indication that you would be down to try this again. You've done all the work so far, and I thank you for that, on behalf of hopeless goons everywhere; now all you need to do is give him any kind of signal at all that you're still interested. Make a joke about it if you want ("We should go to Starbucks so I can spill coffee on you this time!") or just don't mention the awkwardness at all and ask him if he's busy this weekend (or whenever). He should pick up the slack at this point. If you think you've made it absolutely clear that you're still interested, and he never actually takes the initiative, then I've misread his continued staring, and his apology, and he is just a very confusing gentleman. My guess is that he would know how to deal with 1.) you not liking him or 2.) him not liking you, but what he got was 3.) an unreadable situation because the date got soda spilled all over it and became illegible. If you establish your (continued) interest, I think he'll take it from there.

Topics: Life
Tags: dating, crushes, dates, awkward situations, advice, ask jono

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