Dear Captain Awkward–
I’ve been doing pretty well in the online dating world. Guys initiate things with me, I initiate things with girls (apparently that’s how bisexuality plays out on OkCupid! Gender stereotypes! I have them!) and I’ve been on several good dates. But it’s my first OkCupid date that sticks with me. An artist at a nearby college, in the process of coming out, short, funny…but I felt that I was much more into her than vice versa.
It’s been a couple of weeks and we haven’t hung out since that first awkward/fun but clearly-not-happening-again date, and our texting petered out after about a day. I’m a bit disappointed by this, but not, I think, overly invested. I’ve even dated other people!
Here’s the question: I’d kinda like to text her. I’m not sure why–or even what to say–but I’d like to know her better. Talking to her is fun! And on the profile she said she wanted friends! But. Have I been rejected? How can I open up a friendly conversation with her? Should I?
Not A Deep Question. But I’d Like To Know!
Hello, Not A Deep Question!
Thank you for a question to ease me back into posting after a break to wallow in freakish misery with a sinus infection this past week.
First, my hang-ups: I’m a bad person to ask about texting, because I am prickly about it. It’s an incredibly useful timesaver, but if you’re texting me, it had better be “about” something and/or you had better be inside my inner circle. When online dating, I will often provide my phone number when the first date has been scheduled as a “Ok, call or text me that day if plans change or you’re running late” safety measure, but woe betide the person who takes that as an invitation to become my Shiny New Texting Buddy. Negative 1,000 points if you text me with the word “Hey” and nothing else. It’s not my Chief Flirting Medium, in other words, and I find it kind of intrusive when it’s someone I don’t know all that well. So when I encounter an Exuberant Texter (or the constant IM-er) I sometimes have to say “Thanks for the texts, but can we save it for the date?” or “Sorry, I can’t talk now – can you email me instead?” and if they don’t listen to me and keep texting they get pre-dumped before I even meet them for being a person who can’t hear a no. Negative one million points if they text me things like “Was just trying to show that I liked u, what’s wrong? U need 2 loosen up.”
I realize that that’s just me! I am old, prickly, and uptight! I need 2 loosen up! It’s also a “gut” thing – if the attention feels intrusive and annoying vs. exciting and easy that’s telling me something and I pay attention to it. Edited to Add: For me, switching from email to texting is like going from the vous to the tu in French (or usted to tu in Spanish) – you need to be at a certain comfort level to be invited! [/edit] So this is why I will argue that if the date didn’t really spark and texts petered out, texting her is not the way to go. Use email to reset the relationship and ask the question you really want to ask. And if you want to hang out, find some specific event that you think she would like.
“Dear ____, it was really fun to meet you the other day. I couldn’t really tell if we hit it off romantically, but you are so cool and I liked talking with you so much – would you be interested in hanging out again sometime? There is this ___(event/place) I think you would really like. Let me know.”
And then you wait. If you don’t get an answer, that IS an answer. If she was into you (keep in mind, she’s only newly coming out and maybe new at any kind of dating) you give her an opportunity to speak up, and if you’re meant to be friends making the transition will be fun and effortless.
Finally, if you’re into dating men as well, consider making the first move with men you find interesting. Make it a less gender-stereotyped world, ok? This most recent dating experience put you in the “dude” role of making the first move and making the followup moves and trying to read the signals and figure out whether someone likes you or is blowing you off and wanting to contact her without setting off her personal tripwires. How do you like it? It’s awkward and weird, right?
Ok, good talk. Go forth and send a short, friendly email.
CaptainAwkward.com 
Love it.
Firstly, may I say that I am also old and likely need 2 loosen up? I generally don’t even carry a cell with me (and I’m under 35, so just an outlier Luddite) and I HATE texting except for finalizing and confirming plans and/or travel arrangements.
But I love the terror of asking someone out. Rejection stinks, but it is so so so so so much better than waiting around to find out if someone else has noticed/is interested. Not that it’s not great to be asked out by the person you’re working up the courage to ask, but I’ll take control over passivity any day.
Also? I will take frank questions and answers over wondering forever. LW? Just ask. And not via text. We can all use friend potentials.
Good advice, but as a person who does actually like texting, I’d like to weigh in on the texting/email thing.
I like texting, maybe because, I dunno, I get the feeling that it was a Thing in the UK before it was in the US? I mean, when I was a teenager me and my friends communicated pretty much solely by text, because it was cheaper than ringing someone’s cellphone and mobile email hadn’t really been invented yet. I also really dislike phonecalls – for pretty much the same reasons that you hate texting, Jen. I don’t mind phonecalls from people I am close to or phonecalls from people who need to *tell* me something, but if somebody I don’t know that well rings me up “just to chat” I tend to get skittish. Now that I’m abroad most of my communications with friends who are not directly in front of me take place via email, mobile email or Skype, but when I’m in the UK – I’d much rather get a text or an email from somebody I don’t know that well than a phonecall. Apart from anything else, a text message is something you can ignore and come back to later and isn’t going to get you in trouble if you get it in class.
That said, not everybody likes being texted, the same way I don’t really like being called, and if somebody keeps calling me when I’ve made it clear I’d rather they texted or emailed me then, as you said, that’s a sign that this person does not know what “don’t do that” means. Maybe this girl doesn’t like texting from people she doesn’t know well, for whatever reason, and so trying to re-establish communication via email might feel more neutral to her, and it’s a good idea.
…yes. I guess what I’m really trying to say is that you’re not coming across as needing to loosen up! (And also, I hate text-speak and always have and now that phones come with qwerty keyboards THERE IS NO NEED FOR YOU TO BE DOING THAT ANYWAY STOP IT STOP IT STOP IT.) Methods of communication can be weirdly tricky.
I also don’t like talking on the phone that much, especially when it’s the cell-phone call of “I’m bored…amuse me!”
I’m glad you said something about living abroad – I see texting as a bit less formal than email, so switching between email as a form of conversation and texting is like going from the vous to the tu in French (or from the usted to the tu in Spanish) – if someone makes the switch before I’m ready or before they are invited, things get a little awkward. It’s not the end of the world if they do, but it makes me a little on edge.
I agree that texting might not be the way to go in this situation, and not because I don’t like texting (I do, actually). But I see texts as best when they’re short and quick, like when you make plans or need to give someone some other short and quick information. I’m not a fan of getting texts that are more than a sentence or two (maybe because I have an old phone and scrolling through is annoying). Re-opening communication lines is usually the sort of thing that you need at least an introductory sentence for, so email is probably better for that.
If you’ve kept in contact with her at all since you last saw her, I think it would be okay to send a short text saying something like, “Hey, I’m going to ______ (event that you actually think she’ll enjoy) this weekend (or whenever). Want to come?” But if you haven’t really said anything to each other since then, I think the email script that the Captain gave you is probably the way to go.
I definitely agree with this. Coming up with a specific plan is a great idea for keeping someone from wondering “why this text? why now???”
Also, yeah, coming out time tends to be Awkward Time Squared, at least as I have experienced it second hand in terms of my friends. So if she is not interested, doesn’t respond, acts like you are doing something weird by asking her out again etc, don’t be like OH GOD WHY, I FAIL AT THE LADYSEX. Honestly, she is probably going through some complicated things right now, and may not be quite as ready to date as you probably hope.
Actually, I would pull back a little bit more and ask yourself, does she want to be contacted by me right now? Sometimes we are insecure and oblivious, but most of the time if you feel like it’s not working, I’d go with your gut.
1) Be honest with yourself about what YOU want. Do you want to be just friends forever with this person? Could you be totally cool setting her up with someone else someday? Would it freak you out if your bestest friend in the whole wide world dated her? If the answers are yes yes YES and duh, then friends is a great idea. This step is so SO important, by the way, because no matter how hard you try, someday your friends may all meet one another and you don’t want to end up with a situation like this one (http://therumpus.net/2011/09/dear-sugar-the-rumpus-advice-column-85-we-call-this-a-clusterfuck/).
2)Ok, so it turns out that the thought of her dating other friends of yours makes you squeamish and you are really coming from a place of, “I like her and I want her however I can take her!” If you are interested in her in a non platonic sense, let her know right off the bat instead of going the “she will realize I am right for her someday, I can feel it!” route. Seriously. Not a great idea but so many people do it! Why!
Whatever you decide I like the Captain’s suggestion about a “reset” with a no-pressure email where you tell her 1)you had fun and you would like to hang out with her sometime AS FRIENDS or 2)you are interested in seeing her again; is she into that?
Then, lay low, back away, and let her think about it. If she never responds ever ever, it sucks but there is your message. Either way, don’t wait around for her to make up her mind! Go on lots of dates and have an amazing life. She can be a part of it if she wants, but you’re down either way.
I actually have to disagree with the Captain here. You went out on one awkward, clearly not happening again date, and sent a few texts back and forth the day after until they petered out (just a guess: was she the person who didn’t respond to the last text?). It’s been weeks since you last heard from this girl. I think you already have an answer.
You’re going to meet a lot of people through online dating. Some of them won’t be into you, and you won’t be into some of them. And although being totally clear with people about whether you’re into them is generally the best policy, sometimes you let things peter out with the understanding that no communcation sends the same message.
And the thing about online dating, if you don’t mind some friendly advice from someone who also finds it really awkward but is trying to do it anyway, is that it’s important to not get invested in the people you like until you get past a second or third date. The online meat market depersonalizes things a lot — you don’t have any investment in a person until you actually meet them in real life and see whether you click. And it’s a lot harder to make a transition from potential romantic partner to friends if your only interaction with someone was a blind date.
Basically, my advice is this: forget the short, funny girl who didn’t seem that into you. There are tons of people out there who will be into you, and when you meet them, you won’t be left wondering whether or not they want to see you again.
This is definitely one possibility. For some people, saying “I’m not interested” is unthinkable, so they do the slow fade.
But I don’t think it’s the only possibility. I briefly dated one man who I had a fine time with, but he was very slippery about making another date and backed out of the dates we did make. I told myself that I had my answer, and started seeing someone else. Then, the first guy got back in touch and wanted to hang out. I told him I was no longer available, and he wished me happiness but expressed disappointment that we hadn’t worked out, because he thought I was pretty great. This was astonishing news.
It didn’t change anything, though, because I then knew that this guy was someone who (a) wasn’t very reliable about making and keeping plans even when he liked someone and (b) he wasn’t very verbally affectionate. Dealbreakers, for me.
That’s why I approve of asking – no matter what, you’ll learn something. Possibly an excuse to move on.
I agree with tanglethis – it’s important to hear and respect “no,” but if you’re in the pursuer role (as it seems you are here, LW) you should wait for an actual “no.” Doesn’t have to be a verbal “no” or an unequivocal “no,” but you should wait until you’re satisfied the answer is really “no.”
Dating can be a bit like trying to find street parking in a crowded city – you can get to the point where if you see a space, you just assume it’s not legal parking because otherwise somebody would be parked there. Probably true a lot of the time! But if you adopt that attitude… you’re never finding parking. So read the signs, and wait for “no.”
The Captain’s personal texting aversions aside, this is quality advice straight from the dating canon. (As opposed to the dating cannon, which I’m now trying to construct in my mind.)
You aren’t sure if things are groovy, so you ask. An answer will clear things up and silence will, too, and then everyone knows what’s going on without speculation and what-ifs. Win all around!
For what it’s worth, I would also go the email route; there’s too much going on for a text, and phones demand immediate response that freaks people out. I don’t think HusbandLogic and I talked on the phone more than 5min throughout our courtship, but the chat logs and email threads are epic. Nothing makes HL clam up faster than the idea that he has to say something, anything RIGHT NOW. But give him a minute to compose and type, and he won’t shut up.
What I’m sayin’ is, your mileage is gonna vary, but a non-pressuring email is your best bet for this situation. Have a blast dating all the people you can and want to date! 😀
Hey, thank you all for your great advice. Can I just ask one thing? What the fuck does LW mean?
You’re welcome. Letter Writer.