Dear Captain Awkward,
First off, I have to thank you for Reader Question #3: A shy guy I like caught my eye. For most of my adolescent life, I was just like you. My love life was a trainwreck. I had confidence and self esteem issues because I thought I was unsexy and therefore unlovable. (As I’ve gotten older I have realized I am actually a kickass smart sexy lady.) For most of my life I followed the approach you described: starting with a crush, ending in insane FEELINGSDUMP confession, usually via letter. I always hated myself for it and assumed I was crazy. My friends tried to help me, but for whatever reason, their advice (just talk to them, they’re just a person) just didn’t stick.
That was me, up until I turned 20, when I got involved with a wonderful guy. Said guy had been my good friend for many years, so it was easy for me to ask for what I wanted. We were living in different states for awhile, but eventually I moved to the same state, and we moved in together. That relationship has run its course, and we separated on good terms. Now, at age 22, I am finally ready and confident enough to try dating. Only problem is I’ve never done it before.
I have recently developed a crush on a cute guy who is an acquaintance. We were friendly, but we hadn’t hung too much, although we’d talked about playing music together (he and I both play guitar). So I followed your seven step plan and it worked! You have no idea. It’s changed my life. For the first time ever, I chilled out! I Used My Words, I asked him out for sushi, and it was great. The conversation was good and we have lots in common. We discussed the possibility of hanging out again soon, and I think we will. The only problem is, I’ve never really dated people before, so I’m not sure a) what is an appropriate amount of time to wait before asking him out again, and b) if he might be interested in dating me. My friend asked if we were flirting, and I honestly wasn’t sure. I think so??
My question to you is, how can I make my intentions clear to this guy in a casual way? Should I just ask, “Hey, cute guy, just curious, but do you have a girlfriend?” I am pretty sure he doesn’t, but I can’t figure out how to go about telling him, “Hey, I like you, you are cute, nerdy and sweet, and I would maybe like to date you!” Also, how long should I wait before I ask him out again? Is a week an appropriate amount of time, or maybe two?
Thanks for reading.
Signed,
Was that a date?
I’m glad that using your words got you this far!
I recommend that you keep doing that. Since I’ve sat on this question for a couple of days, I’m hoping that a flurry of texts/Facebook messages/emails have solved this question already? In case they haven’t, may I suggest “I really had fun with you the other night. Can we do that again soon?” for the words, and “Whenever you feel like asking him, unless he asks you first, preferably soon” as the ideal timeframe. A week or two? For 22-year-olds with cell phones and internet access? That would have felt like a long time even in 1996 when I was 22. If he had as good a time as you and is thinking along the same lines, I promise it will be very very very very easy to make more plans. If he’s evasive, slow to respond, and/or it’s hard to set something up, pull back.
And if you’re feeling brave, get right to the point:
“I had a great time with you the other night, and think you are cute and nerdy and sweet and that I would maybe like to date you. Can we make plans to hang out again very soon?”
And if he says no, say, “No worries! You are awesome, so I had to ask.” Then change the subject back to something very innocuous as a sign that you will not make him have long awkward conversations about this every time you meet.
You got this! Let us know what happens.
CaptainAwkward.com 
Yup, that’s just about perfect.
Basically, you will know if he likes you if it is easy to make plans AND he initiates contact with you as well. “Like” should be reciprocal to be pursued. Go for it!
(and if you really don’t know, ask. I had to do that once because I was SO CONFUSED. It was a date. It was a pretty decent short relationship that I’d never have had if I had not asked.)
“You are cute and sweet and nerdy and I have the biggest crush on you. Would you like to go out?” is how I have gotten into literally every relationship. Never underestimate the direct approach.
Keep on keepin’ on! And there is no shame in saying “Just to be sure we’re on the same page, this is a date. Like a DATE date. Yes?”
And then he will either be like “YES, and I am so glad you said because I didn’t know how to. You are so good at words!” Or he’ll get weird and you can be awesome and cool and like “Oh! Welp, glad I asked! Let’s sushi/concert/whatever-we’re-doing and call it a night,” like it ain’t no thing. ‘Cause it ain’t!
And if you ask him and the response is negative, don’t feel obligated to be friends. Unless you WANT a new friend. 🙂
Why are these posts always so timely? I’ve had a few “maybe dates” with the sweetest, smartest lady recently, and I’ve been poling my friends about when I should ask her out for realz.
*Prepares to use her words like a BOSS.*
Perfect answer. And don’t wait for the follow up. Funny story: Years ago, I met a friend of my friends–thought he was cute, kinda liked him, wanted to date, but didn’t want to put him in an awkward position. So I asked our mutual friend to see if he’d be okay with her giving his email out. She emailed me back with his email and said he was totally fine with it–I shot him a message and said that I enjoyed meeting him and that I’d love to hang out with him if he’d be up for it. He was. Funny thing–I got overwhelmed with work and couldn’t email back for a few days, and I got a follow up email from him. “Hey, Sheelz, anytime you wanna get together, lemme know.” So I did and we did and we dated for about a year and a half (parted sadly but amicably).
LW here, the guy seems to be unable to pick up his phone, so I’m pulling back. Sorry I got all your hopes up! Hey, this is a perfect time for me to try my hand at internet dating. Thanks for answering my question.