#229: You must chill (online dating edition).

John Cusack holding up a boombox in Say Anything
Back away from the boombox, Dobler.

Dear Captain Awkward,

I’m a serially-single female in my mid-20s who has only been in two relationships. The first was when I was 20 and lasted seven months and the other was a on-and-off disaster that ended a few months ago. At the encouragement of my friends. I entered the world of online dating. It wasn’t my first time online. I’ve gone on a handful of online dates over the past few years and that have never resulted in a second date.

Until now. Somehow the first person I decided to have a conversation during my most recent fory turned into a good date, and now a good series of dates. We’ve already entered the hairy business of talking about our past failed relationships, our family, our habits etc. It’s only been five dates over three weeks, but to me it feels like I’ve known him much longer. Everything has been going well and for the first time in a long time I feel like I’m getting attached.

Yesterday out of boredom I signed onto the dating site where I met for the first time in a long time. I’m pretty savvy with my online privacy settings and avoided clicking on his profile, so he couldn’t see that I had visited it. However I did manage to see that he was “online now.” Since then I’ve gone on twice since and seen that he has logged on twice since as well. We have never had a talk about exclusivity, so this is all fair game.

Seeing that he was online hurt me and threw me a little. Since we met, I’ve all but stopped browsing on the website. I’ve logged on occasionally to read messages people have sent me and browse out of boredom, but I would describe myself as no longer actively looking. I’m fully aware of the irony of this, being that I had to be online as well in order see him. But my intention wasn’t to cruise other people? It doesn’t help that he’s been in many long-term relationships and doesn’t do one-night stands. He’s only been kind, open and considerate towards me so I’m worried it means I’m not enough relationship material for him.

This is going to sound weird and maybe a little conceited, but I’ve never been the one in the relationship to like the other person more than they like me. I’ve never had to initiate the “Where Is this going” talk. However, I have been a little freaked out by this talk before, which is why I dread having to start it. And knowing that he’s still browsing, I feel reluctant and fear I know the answer already. My friends think it’s too soon for me to bring it up and think that I should be making the most of the online dating world by seeing other people too.

Am I making a mountain out of a molehill? Is there a way for me to bring this up that will not result in the “relationship” talk? Or is it just time for me to deal with the inevitable conversation? Do you have any advice about how to start it, things to avoid, or things to definitely bring up in this talk?

Thanks Captain Awkward.

I do have some advice.


One, as you mentioned, you see him signed into the dating site only when you are also logged into the dating site. The Gift of the Magi keeps giving, apparently!

Two, sometimes people have their settings turned on so they get an email every time someone messages them. So you click a link and whoops! You’re logged in. Checking out who messaged you gets to be a habit, does it not? Curiosity! Affirmation of your own attractiveness and desirability! A message that makes you ask yourself “What fresh hell is this?” and submit it to the An(n)als of Online Dating! (That link is safe for neither work nor eyes).

Three, often we correspond with and casually date a few people at the same time. He may indeed have settled on you as the person he wants to date more exclusively, but needs a little time to politely phase out communication with other people that he genuinely likes. Both Commander Logic and her awesome husband went on dates with other people after they first met and liked each other. It didn’t make them not like each other, it made them say “Oh wait, I choose YOU.” So, going back to point one, Dramatic Irony, he may be feeling exactly as you do: Into you! But feeling like he needs to keep his options open for a little longer. And wondering “Hey, what’s she doing online?”

I feel like I had a very similar situation/conversation a month or so ago, where I knew that the person I was seeing (am seeing) was going to be important to me and I didn’t feel like writing back to a bunch of nice dudes saying “Hey, thanks for your nice note. Unfortunately(?!?) I just started seeing someone really great and want to see where that goes, but if it doesn’t work out, yeah, let’s get a drink sometime!” So I disabled my profile and stopped logging into the site. Until we figured out what we wanted, he was free to do whatever he was going to do, and I was free of driving myself nuts wondering about it. I was also free of expending energy on “keeping my options open.” That stuff is time-consuming, yo! If things didn’t work out, I could re-open my “options” at any time. In the meantime it felt great to be sure of my own feelings – “Okay, I know I’m IN. Let’s see what happens.”

There’s something in there, I think, about making romantic choices from a place of confidence and abundance rather than the feeling of scarcity. You both have other options and know that you do. If you both choose each other, you can feel pretty confident about the choice.  People who like you will act like they like you; it will be easy to communicate, to make plans, to talk about stuff. It sounds like this guy likes you. There’s also something here about timing. People don’t fall in love with each other at exactly the same moment.

So, chill out. Remind yourself it’s only been three weeks. Temporarily disable your profile and make a decision to stop tracking his online activity. Spend time with your friends. Channel that anxiety into work or school or exercise or art projects (but not art FOR or ABOUT him, aka, FEELINGSART).

That doesn’t mean that you shouldn’t express your feelings. This thing where people are actively looking for love and connection but they only get it if they pretend really hard that it doesn’t really matter and play it cool all the time? EXHAUSTING BULLSHIT. But I strongly suggest that you go with “Hey, I really, really like you and dating you is making me really happy and hopeful,” vs. “Why are you looking at other girls? Are you looking at other girls? I can see that you are probably looking at other girls.”

That vulnerable anxious feeling you have, like, this is really really good and suddenly there is something to lose here and you don’t want to lose it? You don’t get to the good parts of love without going through a little bit of that. Go ahead and be vulnerable. Give the guy a little breathing room to figure out his own mind, and trust that someone who likes you will do what he can to let you know and reassure you that he likes you. If a couple weeks from now, you’re still feeling anxious and unsure? That talk goes something like “Hey, I really like you and I’m pretty sure I don’t to date anyone but you. What do you think about that?

If it doesn’t work out, you have options, and the same good qualities that made this person like you will attract other people. But if this is good and is making you feel good? Trust in that enough to give it a little time. Nothing good gets away.

8 thoughts on “#229: You must chill (online dating edition).

  1. DO NOT BRING THIS UP. The fact that he has logged onto a dating site? Is not relevant to your interests.

    He likes you enough to want to see more of you. You would like to see more of him. You should keep seeing each other. At some point, if you continue to like seeing each other and wanting to see more of each other, one of you will use your words and express that you only want to see the other person, at which point the other person will hopefully say “me too!” Or maybe “I like you and would like to keep seeing you, but I don’t think I’m ready for something exclusive” or even “you’re a lovely person, but I don’t think we should see each other anymore.”

    Notice that none of those scenarios have anything to do with whether he has been logging onto an online dating site for any purpose. Because down the line he will either want to get more serious with you or he won’t, and you two will need to work that out based on a conversation with each other and your feelings. If he wants to get more serious, then the fact that there are seventy billion people posting pictures of themselves online isn’t going to matter. And if he doesn’t want to get more serious, the fact that there are seventy billion people posting pictures of themselves online won’t be the reason. And while it might feel like a good way to figure out what he’s secretly thinking about you, the Captain pointed out the multitude of ways in which it is a ridiculously bad measure of that.

    The only, only way I could see him logging onto a dating site affecting your relationship with him is if you let it get in your head and then bring it up with him and then he thinks “yikes, why is she monitoring my online activity and acting like I owe her an explanation for it after a few dates?” And that will probably not be the effect you want it to have. Focus on how he treats you when you’re together, and whether he stays in touch in between dates, and how you feel about him. That’s what’s really going to tell you where this is going.

    1. “The only, only way I could see him logging onto a dating site affecting your relationship with him is if you let it get in your head and then bring it up with him and then he thinks “yikes, why is she monitoring my online activity and acting like I owe her an explanation for it after a few dates?” And that will probably not be the effect you want it to have.”


      I mean, the whole comment gets a big “YES, CORRECT”, but this in particular. I would dump anyone who made it clear they were monitoring me in this way this soon into a relationship because it communicates “needy and controlling.”

      You can FEEL needy and anxious? Absolutely. But you choose how you act on those feelings and think about the effect your actions have on other people.

  2. My partner and I have been together for about half a year, and we met on a dating site (I’d guess it’s the same one as the LW is using because it’s free and actually better than the majority of pay sites). We’re very happy together, and we had the “relationship” talk after about 3-4 weeks, which basically went, “I’m not seeing anyone else and I don’t want to, and while I’m not ready to start calling you my boyfriend/girlfriend, I want to be exclusive.”

    After that, both of us (individually, this wasn’t something we had agreed to do or asked the other to do) changed our statuses on the dating site to “seeing someone.” About a month later, I was getting annoyed with all of the, “Hey, someone’s checking you out!” emails, so I disabled my account.

    My partner still has not disabled his account. He still gets emails when people “check him out” or message him. There are two reasons I don’t really care. The first is that I actually find it really amusing and wish he would let me read some of the messages because I get all, “Ahaha, ladiez, this wonderful man is not available!” (He doesn’t want me to read them, so I don’t ask anymore). The second is that he’s actually met friends through the site before, and so on the off-chance that he has an opportunity to make more friends, he’s not disabling his account.

    The point? LW, you are 3 weeks in, and it sounds like things are going very well! If you’d like to talk to your potential partner about exclusivity, now isn’t a bad time. But you have to chill about the online dating thing. It sounds as if you’re reading too much into everything, and that there really aren’t any legit red flags.

    I had a lot of first and second dates with online dating that just fizzled out. I’ve had some really unhappy relationships. What makes it harder when you find someone with lots of potential is to bottle everything up and read too deeply into everything, and second guess how something good could be happening to you. I don’t advise a FEELINGSDUMP, but definitely communicate calmly if something is really bothering you.

  3. It also depends on the dating site, to be fair. I’m a member of OK Cupid, and have been throughout one long term relationship. I kept my profile on there because a) there’s cool quizzes; b) there’s a social network there (both through journals and forums) and keeping membership was the easiest way to maintain some friendships) and c) there’s a setting for ‘Seeing someone’ in the profile. The important point was that my partner knew about my membership of the site throughout.

    1. Agreed. I finally deleted my okcupid account because I didn’t have the energy/desire to continue talking to people there, but I was active on it throughout a couple relationships (with their knowledge, and the ones I met from okc kept their accounts open as well) because I had met awesome people that grew into friends from there (with non okc ways of getting in touch). And some of the forums and quizzes amused me. And some guy clued me into my city’s queer softball league through a message there. Some online dating sites have a lot more than just “dating” going on on them so I wouldn’t worry too much about this dude’s continued perusal of the site right now (in addition to everything the captain said).

  4. My sweetie won’t let me delete my OKC account because…I’m not sure why. So he doesn’t feel weird and lonely being on it?? I mostly ignore it now in any case. Anyway!

    New relationships are a worrying quagmire of “Do they like me? Do they like me like I like them? What is going to happen?” I have been getting to that point. And I get the butterflies and weebles, but it’s not like it’s a secret ballot. I can see he likes me. He does stuff that says so. He’s considerate. He’s excited to make plans.

    Does your dude show that he likes you? If so, relax! Have The Exclusivity Talk, and be nervous (it’s a nervousy thing, being vulnerable enough to like somebody)…but you don’t need to sabotage yourself.

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