ShyGuyFilter: What's my next move with an unassertive guy?
September 21, 2008 9:16 PM   Subscribe

I initiated our hang-out; he enthusiastically responded. The evening started with great conversation and mutual interest-- and then the energy seemed to weirdly wane as the evening went on. To be fair, we had a grueling evening. What now?

At the risk of posting another "Is he into me?" question, here goes:

I met a guy through mutual friends a couple weeks ago-- I was pretty smitten, and he didn't leave my side all evening, kept asking me questions, giving me cute looks. We talked for a couple of hours and there seemed to be a real connection-- we had a ton in common, and I found him instantly intellectually engaging. He facebook friended me within hours, and I (uncharacteristically) asked him out. He responded enthusiastically right away, and we made plans to go to a theater festival later in the week.

So the big night arrives, we go to dinner, and everything's going great-- he's looking foxy, the convo is easy and flirtatious. All's well. Then we go to one show, which is great, but long. Then we go to another, also long and demanding. It's getting late, and I'm starting to get tired. The convo is still good, but it feels like we're both getting worn out. We go to a few more shows, and he finally brings me home around 2. We're both exhausted at this point, and we chat awkwardly in the car for a few minutes before I say, "Okay, well, have a great day tomorrow" and bolt.

A few additional facts:
- He told me a few times throughout the evening that he's extremely shy and unassertive, made reference to being a big nerd back in the day.
- We accidentally touched arms a few times, but he didn't let it linger.
- I ran into him several days later and he was friendly and seemed a little nervous. I didn't say anything about hanging out again because I just can't get a read on him. We had a friendly casual chat, and I left being more confused than before.

Question: Did I screw things up by having such a long, grueling first date, a multi-hour event that might exhaust any two people who don't know each other well? Should I hang back now and wait to see if he initiates something? Is he interested and deadly shy, or simply uninterested, and I'm in denial?

I usually just scratch someone off if they're not enthusiastically initiating plans, but maybe he's just really shy? Help!
posted by anonymous to Human Relations (22 answers total) 6 users marked this as a favorite
As a used-to-be shy, used-to-be geek, if he seemed "friendly and nervous," I'd say it's because he doesn't know how to tell you what a great time he had.

Ask him out again. If you're really concerned about the gruelling nature of your first date, make it into a joke, something like "Maybe this time we only run half the marathon, ok?"

Good luck.
posted by ZakDaddy at 9:23 PM on September 21, 2008 [5 favorites]

If the date happend "a couple weeks ago" and you haven't talked to him or hung out for a few weeks, you may be close to missing your opportunity- a lot can happen in a few weeks, including him totally writing you off as not interested) so don't wait any longer. I don't see any reason why you shouldn't ask him out again, if you want to go out with him again. If he turns you down, oh well, at least you'll know.
posted by ThePinkSuperhero at 9:23 PM on September 21, 2008 [3 favorites]

we chat awkwardly in the car for a few minutes before I say, "Okay, well, have a great day tomorrow" and bolt.

Sounds like he was waiting for you to ask him up*, and when you didn't, he thought it meant you didn't like him. You can recover but definitely you'll have to reach out to him.

*I'm not implying he was after sex, but usually (in non-Utah parts of the US at least) after a successful first date you invite the person in for coffee or something, even if it is literally just coffee. To someone who's maybe a bit shy, "bolting" could send a strong "not interested" message.
posted by drjimmy11 at 9:30 PM on September 21, 2008 [1 favorite]


>he's extremely shy and unassertive
>he didn't let it linger
>I didn't say anything about hanging out again

He was too shy to make a move on you... and he probably thinks he's blown it with you.

Just ask him out, and, if the idea doesn't bother you overmuch, make the physical advances yourself.
posted by darth_tedious at 9:31 PM on September 21, 2008 [3 favorites]

If you were tired, he was probably bushed too. Ask him out again (for a shorter date) and then bring him upstairs for a nightcap.
posted by The Light Fantastic at 9:53 PM on September 21, 2008 [1 favorite]

I sound exactly like him when it comes to dating – shy, unassertive, praying that she would make the first move, and so on. I’m guessing that he probably thinks he blew it and is waiting for you to show him some sign that he did not.

Your first date with this guy was probably going to be grueling for him no matter what you did and since you did something that was grueling…well, it was probably quite intense for him.

Give him a call and do something extremely low key, like a movie at your place or coffee/drinks downtown. It sounds like you might have to take the initiative and show him that yes, you’re into him and yes, it’s ok if he holds your hand / has physical contact with you / etc.

Good lock!
posted by Diskeater at 9:59 PM on September 21, 2008 [1 favorite]

If you figure the guy to be shy/reserved/unassertive, during the process of the first date, he might have encountered something that caused him to lose confidence... and thus, sort of lose his "groove".

For some of the shier guys, they know they need to be more assertive/outgoing to increase their chances of finding potential partners. What I've found that happens (from personal and observational experience), is that before the date they're nervous as hell and they reaaaaallly REALLY want to put their nice foot forward and try to keep it that way the whole night. However with many people who are shy, there is a lack of confidence so if something happens in the night that might have brought his confidence down (even the slightest bit), he might have been discouraged (and then start a dialogue in his own head about how he screwed something up, which led to another screwup, and how he's letting this thinking distract him, etc.)

On one hand, this guy might be a genuinely interesting guy but be lacking in confidence... or, he might really be somewhat of a shallow guy and sort of fizzled out.

Either way, one date isn't sure enough to know. If you really feel some connection to this guy, I say to ask him out on another date and try not to make him feel/remind him that the previous date was awkward (as someone previously suggested, you can take a humorous tone, which works well with any situation like this). If he takes the offer, then good. If he sort of avoids your offer, it might be that he started losing interest.
posted by NeoLeo at 10:11 PM on September 21, 2008 [3 favorites]

As a guy sometimes prone to shyness around relative strangers, and who prefers for women to be a bit proactive in the early stages of dating, it sounds like you have quite a connection & had a pretty successful sounding date. I can't see any way in which you "screwed up", at least not from the facts you stated.

I'd suggest you ask him out again. Nothing to lose.

(ps - I realise you can't easily respond, but what's with the four or five shows?!?? I'm just curious. Theatre? Cabaret? Drag? Live music? I'm finding it hard to figure out just how anybody can go to that many shows in an evening...)
posted by UbuRoivas at 10:23 PM on September 21, 2008

I hear you about preferring someone showing enthusiastic interest, but some guys just are that shy. While it's possible he's not interested any more, he told you several times he wasn't very assertive. If the long date was as exhausting as it seemed, and if you left as abruptly as you say you did, he may have walked away feeling like a big, boring loser. I'm not trying to make you feel bad. Neither of you were clear about what you wanted, and I suspect he's sitting at home wondering about you, too. But there's a good chance this can be fixed.

Get in touch with him again and ask him out. On the phone or email, don't apologize or rationalize the last date. Just show your genuine interest in seeing him again. And if you do go out again, and if he seems to be as interested as ever, then find some excuse to kiss him early in the evening. Why should either of you spend several hours after all this time apart wondering about the other's intentions? I suspect that if you kiss early, the rest of the date will be much more relaxed and fun. And once things reach that state, both of you can probably talk honestly about your mutual indecision and nerves, then move past that.
posted by wexford_arts at 10:23 PM on September 21, 2008 [2 favorites]

Good news! It sounds like you had the very same first date the missus and I had seven-ish years ago.

Set up another date. Your first one was a marathon and I'm not surprised that nothing happened at the end of it. Not following up with any substantial communication conveyed that you weren't interested. Hence, follow up with some substantial communication!
posted by greenland at 10:40 PM on September 21, 2008 [1 favorite]

Ask him out again dammit! He's waiting for you to call him right now! But my advice, for the second date? No, y'know, six hours of bareback horse-mounted rock climbing or anything of the sort. Whatever happened to cocktails?
posted by turgid dahlia at 10:41 PM on September 21, 2008 [1 favorite]

Sorry, I didn't explain myself all that well before. Shyness or introversion are generally not all-or-nothing affairs. There will be people who you can instantly click & feel relaxed with & chat away for hours, and others with whom conversation is like trying to roll a large boulder up a hill. Probably, everybody finds this to be true, but I think quieter people usually meet fewer people who they can slot into the former category & far more in the latter.

On the bright side, from what you wrote about your meeting & date, it sounds like you're on the good side of the ledger. And what he said about being shy & unassertive? Sounds like a carrot, to me, as if he's saying "hey, can you take some initiative, and I'll happily go along for the ride..."
posted by UbuRoivas at 10:44 PM on September 21, 2008 [1 favorite]

No, y'know, six hours of bareback horse-mounted rock climbing or anything of the sort.

On the other hand, if that's some kind of euphemism, that's probably exactly what you'd be wanting to end up doing.
posted by UbuRoivas at 10:47 PM on September 21, 2008 [1 favorite]

A guy can be shy, and still be a great conversationalist, especially with someone they click with, and it sounds like he clicked with you. Pretty much what other people have already said, the awkwardness in the car was him expecting/trying to build himself up to kiss you, or to make it clear somehow that the interest was more than platonic.

Being that kind of guy myself, if I make a point of telling someone I'm not assertive, it is because I want the girl I'm dating to make the first move, because it takes a hell of a lot for me to do it.

And yep, if I had gone through that awkward car moment and the girl suddenly said something totally non-commital like "Okay, well, have a great day tomorrow" and "bolted," I'd be feeling like a huge loser, and would assume I blew it somehow. Suffice it to say I probably wouldn't call her.

So it is basically up to you now to let him know you're interested.
posted by paradoxflow at 11:03 PM on September 21, 2008 [2 favorites]

I'd say (1) no problems with the long date, (2) he thinks he's blown it, (3) he'll happy hang out again, and (4) he would respond positively to moves, but (5) your chances are slim that he'll make any moves. Why not just invite him over for a movie and make the moves yourself? Btw, he would not have said that he was "shy & unassertive" if he had any obstacles, like another girlfriend.
posted by jeffburdges at 12:02 AM on September 22, 2008

ASK HIM. Get off the internet, pick up the phone and talk to him.
posted by Brandon Blatcher at 3:01 AM on September 22, 2008

I am not shy but at this point in time I am damn sure gun-shy around gals and relationships and stuff, I'm as tentative as an accountant at a whorehouse on Mothers Day, I'm about ready to bag it all and start collecting stamps, or maybe small arms, or maybe stamps with pictures of people with small arms and small hands. Whatever. Just about anything other than to get out and get with another gal and start walking down one path or another.

So here comes Myrtle or Griselda, smiling and waving and gesticulating, and I sortof smile and wave and gesticulate right back at them, and I surely do want to be the sleaze that I am and slide my hand(s) around and find neat stuff maybe but lately it seems I find myself hurtling out of the room, I suspect that I'm screaming as I go but I don't know exactly, it all happens so fast, it's surely out of character for me, or for the character that I was anyways.

Hurtling is a great word.

It sounds like an Olympic event -- "Okay, and now it's over to Melvin over at pavilion B for the Men's Competitive Hurtling event."

So maybe your friend has gotten hit by some of the same relationship buses that have hit me, maybe he's shy like I am just now. Not having been through this before, I can't exactly give you advice on how to negotiate the terrain, you might want to toss him pieces of bread like you'd do for a duck or a goose at the pond in the park, slowly and gently gain his trust, but please please please don't do this if you intend to catch him and eat him; I'd hate to think I had anything to do with anything like that.
posted by dancestoblue at 3:05 AM on September 22, 2008 [10 favorites]

Oy just seriously ask him out already. If he is rational and even semi-into-you, one tiring date won't be enough to screw things up. Really. Ask. Him. Out.
posted by nihraguk at 6:43 AM on September 22, 2008 [1 favorite]

you asked him out once, just ask him out again. he can say no if he wants to.
posted by misanthropicsarah at 8:06 AM on September 22, 2008

Women often measure a guy's interest via how aggressive he is. But the thing is that in reality we're a lot like you and aren't sure what we want a lot of the time. From what you describe, it sounds like he's interested but needs a push. You give it to him. Ask him out again and avoid the shows and only go to dinner. Touch him on the upper arm some. See how he responds. If you feel like it and he's into the touching, at the end of the night initiate the kiss.
posted by Ironmouth at 9:51 AM on September 22, 2008 [3 favorites]

Ask him out. Right now. Then comment here and let us know how it went! We're involved now.
posted by misha at 11:18 AM on September 22, 2008

Follow-up from the OP:

Thanks for the encouragement. He actually *did* get in touch, and we have plans in the works. I'll keep you posted. And again, thanks for your wonderful, metafiltery wisdom. I do forget that some people are really, really tentative, and it certainly doesn't hurt to extend myself an extra several feet (or yards) to help things along. :)
posted by jessamyn at 5:39 AM on September 27, 2008

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