Dear Captain,

I am a man and I have a problem: I’m a creep.

I’m 30 years old, and I haven’t had a whole lot of romantic experience. I’ve been shy my whole life and dealing with anxiety and depression since my teen years, so I haven’t put myself out there as much as I could have, and haven’t had the self-confidence to be a good prospect in the past. My social skills have been getting better, and I’m getting treatment for my mental health issues. I think I’m capable of dating now, and I’ve met a few interesting women to connect with in the last year or so. These days, I even manage to gather up my courage and ask them out/confess my feelings. However, I never to seem to get a straight “yes” or a “no”, and I end up responding in a bad way. Some examples:

I met a friend-of-a-friend a few times before, and we had flirted with each other, so I was feeling confident about our connection. Our group went to a party a while back, and I ended up asking to kiss her when we alone at one point. She said “I don’t know” and it looked like she was nervous and didn’t know what to do. I backed off physically, but I pressed the point: mostly questions in the “why not?” vein. We parted without incident, but met back up at the end of the party (the group was riding back together). For some reason, I tried to flirt some more, and I just ended up creeping her out. I’ve had enough self-awareness to keep my distance ever since, though the damage has already been done.

Another scenario: I saw a woman on a regular basis at an activity. I liked her, and told her so one day. Confronted with the news, she became very awkward and didn’t give a clear verbal response (“oh…uh…”). We ended up having a good conversation (about

everything else), but my declaration was left hanging. Before I saw her again, I e-mailed her to ask to talk again—I had been flogging myself for not knowing what to say. Her response was a clear “no”, and it was obvious that my e-mail had been unwelcome. I was glad to get the straight-up answer, but I had to push her boundaries to get it.

There have also been a couple of recent instances where I’ve asked a woman out and didn’t take her “I can’t make it” as an “I don’t want to”, and have ended up pestering them again.

It’s clear that I’m establishing a disturbing pattern: I get interested in a woman; I make a move; she gives a non-committal response; I don’t take it as the brush-off it is and end up making unwelcome contact (i.e. asking for a date again, “but why?”, continuing to flirt beyond its welcome). I know intellectually that getting a non-answer in these situations means “no”. It’s also clear in retrospect that I should’ve just backed off in these cases, but I seem to panic in the moment and not act on that knowledge. Through some combination of wishful thinking, inexperience and brain weasels, I’m pushing women’s boundaries and acting like a creep.

Any thoughts, Cap’n? I feel so guilty about these instances, and I’ve reaped the personal consequences—burnt bridges and cold shoulders—but I’m still not getting it right. How do I remember to bow out gracefully in such a moment?

– Don’t Wanna Be A Creep

Hey Friend, I see you and I used to be you. No, really. Lest we forget, I once left a multi-page letter on someone’s pillow in the bedroom where they sleep.

Media portrayals of romantic pursuit reward persistence. This is doing you (and many, many, many other people) a grave disservice.

You’re not doing anything wrong by asking people on dates, asking them to kiss them, or telling them you like them. There are exceptions – I think teachers hitting on their students is always pretty creepy, for instance, and your cute barista smiles that way at everyone because she is trapped at work and capitalism demands her emotional labor – but feeling attracted to someone and asking them about it isn’t creepy. Also, you are asking, not doing that “making a move” thing in movies where men grab women and mash their faces together that is romantic in fantasy and consensually in established “grabbing” relationships but not actually in real life. So, you haven’t crossed all the way over into creepy. It’s not too late!

So let’s work on your follow-up. Next time you feel that spark of interest in somebody, keep doing what you’re doing and ask. You’re not naturally smooth, so don’t try to become smooth at this. Just be yourself and be direct.

You: “I’d really love to kiss you/take you on a date/get to know you better.”

Nice lady: “Hrm…I don’t know about that.”

You: “Ok! I hope you don’t mind me asking. If you ever change your mind, let me know.”

Your “creep” self-label is probably 99% you being really hard on yourself, but I sense a little resentment or confusion on your part about not getting “clearer” answers. This is actually pretty simple to handle going forward. Treat anything that is not “Yes!!!!!” like “No.” Can’t make it = no. Let me think about it = no. I don’t know = no. Not now = no. You don’t need to push for a clearer answer or settle the question or codify the rejection. Did she say “Yes, I’d love to!?” No? Then drop it. Stop auditing her answers for the yes.

Rejection doesn’t mean you have to hide your face in shame forever or get all weird and Firthy about it, though! Go back to being polite and friendly and never mention it again until or unless she does. You can show that you are safe and trustworthy by being safe and trustworthy. If she flirts with you, it’s okay to flirt back, but don’t renew the request for a date or a kiss. Let her come to you with that. If she doesn’t, that’s your answer.

If it gets too uncomfortable for you to be in limbo with someone, it’s okay for you to pull back on the interaction. Just because you were comfortable with it once upon a time doesn’t mean you have to be comfortable with it when your feelings are hurt.

Women don’t forget when dudes ask them out. We don’t need reminders. If a lady really is on the fence about the whole thing and her “hrmmm…interesting” reaction was a genuine “I don’t know,” she is perfectly capable of coming and finding you later and asking “Is that offer still good?” I once suddenly needed to check my mail in another part of campus at two in the morning so I could keep walking in tandem with the gentleman I was walking home from a party with so we could mutually and consensually maneuver ourselves onto the Couch of Let’s Put On Some Portishead Now That I Have My Very Important Postal Material That Could Not Wait For Daylight. A woman who genuinely wants to look at your etchings will find a way to ask you about them.

You say you are shy and you don’t have a lot of confidence. This is how you build/practice/get confidence: You say your piece, you let the other person make a decision, and you trust that once in a while someone will decide you are worth risking an awkward conversation for. Until that happens, you trust in yourself, in your own worth and good and valiant heart, and pour your love and your time into your friendships, your family, your work, your education, your hobbies, and your community. Live to date again another day.

Another suggestion? Make your date requests more specific. You say you aren’t getting clear yes or no answers, so, make your requests for dates or whatever easier to say a clear yes or no to. “Would you like to be my date to this comedy show on Thursday?” vs. “Can I take you out sometime?”

If the person says “No thanks” that’s your answer!

If someone says no to Thursday, specifically, but yes to the idea, you are cleared to ask again, one time. If it gets super-hard to make plans and it feels like there is never the right time, 1) Stop: “I’d still really love to get together, why don’t you call me when your schedule opens up and we’ll figure something out?” 2) Drop (the subject) and 3) Roll your attention somewhere else.

Maybe someday I’ll stop gushing about Mr. Awkward but today is not that day. He asked me out on Ok Cupid. I said “Yes, but I am sick and busy, can we try this in a couple of weeks?” He said “Sure” and (this is key) then he left me alone. He assumed he was never going to hear from me again and moved on with his life. In a couple of weeks, I got in touch with him and asked him on a date. What if I had never written to him? We might never have met. What if he had written to me repeatedly to get me to go out with him? We also might never have met. Read on for a cautionary tale.

Pickup Artists and other dregs at the bottom of the dating pool talk about something called the “shit test” – where women say no to an early request to test to see if the guy will persist, and they encourage you to push back on this early no. One of my early dating tests that I didn’t realize was a test at the time is the “Hey will this stranger take no for an answer because I kind a need to know” test. I once mentioned to a dude from an online dating site that I would call him over the weekend to confirm plans for a date. Some actual big deal life stuff came up and I forgot to call him. At precisely 9:00 am Monday morning I got a text that said “You didn’t call. 😦” and I had a strangely visceral “Nope!!!!” reaction to reading it, like, ugh, this is already too much work. I was like “Oops, I had some family stuff, sorry” and He was like “My time is very valuable, I don’t like reserving time in my schedule for flakes” and I was like “I hear that, okay, sorry again, let’s skip getting ice cream after all, good luck out there” and then

he

kept

texting

me

all

week

until

I

blocked

his

number

I get from the interactions that he’d been really looking forward to the date and that I hurt his feelings by being less interested. It was probably never gonna happen after that initial 😦 but it was definitely not gonna happen after “Why did you say you’d go out with me if you didn’t intend to follow through?” He was cute and smart and we liked the same geeky stuff but he put my shoulders up around my ears and once they went up they weren’t coming down.

Don’t be Sad Emoji Guy. Persistence is overrated. Pushy people get my back up and if you’re a shy guy who is not very experienced at dating your best dating pool is going to be your fellow shy people who are not so experienced at dating and they are not necessarily going to enjoy feeling hunted by you.

Additionally:

Stop asking for women’s phone numbers or emails when you meet them in bars or group settings. “I’d love to chat with you more, can I give you my info?” Hand them a card (or literally a scrap of paper with your name and a way to contact you on it, please do not overthink this ) . Remove the anxiety of “when do I call/should I call/how do I call/what do I say when I call” from your life completely right now. Change up the idea of pursuit in romance. Whenever I give this advice some dude points out “But he won’t get any calls that way” and it’s like “Maybe not! But if someone does call you’ll know she really wanted to, and in the meantime you made the world suck less by not pressuring women for contact info.” If she loses it, so what. If she doesn’t like your font, so what. The whole point is to stop worrying about it once you give her your info instead of pressuring her for hers. If she met you and she really liked you, chances are she’ll tuck it in a safe place.

for women’s phone numbers or emails when you meet them in bars or group settings. “I’d love to chat with you more, can I give you my info?” Hand them a card (or ) Remove the anxiety of “when do I call/should I call/how do I call/what do I say when I call” from your life completely right now. Change up the idea of pursuit in romance. Whenever I give this advice some dude points out “But he won’t get any calls that way” and it’s like “Maybe not! But if someone does call you’ll know she really wanted to, and in the meantime you made the world suck less by not pressuring women for contact info.” If she loses it, so what. If she doesn’t like your font, so what. The whole point is to stop worrying about it once you give her your info instead of pressuring her for hers. If she met you and she really liked you, chances are she’ll tuck it in a safe place. Don’t be Social Media Hover Guy. Let’s be clear, I would always, always Google potential dates and get an idea of their general online vibe and how well it matched up with what they’d told me, and I think everyone should do this (It’s one way to figure out early on if someone is a Nazi, for instance!) And we’re only human, and photos of our crushes are fascinating. However, when you are trying to connect with someone, don’t monitor their feeds and mention everything they’ve ever done back to them, don’t become the person that “likes” every single thing they say (Really you “like” when I wished my Mom a happy birthday 2 months ago?), DON’T click “like” on all their old pictures. It’s about as subtle as skywriting, and it just feels, as you said, creepy to know someone is monitoring you to that extent.

Let’s be clear, I would always, always Google potential dates and get an idea of their general online vibe and how well it matched up with what they’d told me, and I think everyone should do this (It’s one way to figure out early on if someone is a Nazi, for instance!) And we’re only human, and photos of our crushes are fascinating. However, when you are trying to connect with someone, monitor their feeds and mention everything they’ve ever done back to them, don’t become the person that “likes” every single thing they say (Really you “like” when I wished my Mom a happy birthday 2 months ago?), DON’T click “like” on all their old pictures. It’s about as subtle as skywriting, and it just feels, as you said, to know someone is monitoring you to that extent. Watch for reciprocity. If you are sending 5 emails or texts for every 1 of hers, and yours are like Tolstoy wrote them where she is more Dorothy Parker, ease off a bit.

If you are sending 5 emails or texts for every 1 of hers, and yours are like Tolstoy wrote them where she is more Dorothy Parker, ease off a bit. Read more books by women and take in art by women. If you already read books by women, great? Keep doing that. Ashley C. Ford just had a great Twitter thread on books by black women people are reading & excited to read if you need to refresh your list. Watch movies by women. Listen to music made by women. You want to love women and be with women? Recognize the ways that the world is out of balance for us and look for stories and creative works that address that.

If you already read books by women, great? Keep doing that. Ashley C. Ford just had a great Twitter thread on books by black women people are reading & excited to read if you need to refresh your list. Watch movies by women. Listen to music made by women. You want to love women and be with women? Recognize the ways that the world is out of balance for us and look for stories and creative works that address that. Be politically active about things that are important to women. In the spring it was reported that women are making 86% of the phone calls to resist the current administration’s policies. Do you want to be with women, sleep with women, love women? Have you noticed we’re kinda busy right now? Love us by doing your part so that we can survive and thrive and have some free time to think about dating a nice fellow like you. I will stop adding this advice to dating threads when I see that number move to 50%.

You can’t logick someone into loving you. There is no series of perfectly executed steps that get you there. You’ve reached this moment of self-awareness about what you’re doing and it doesn’t feel good but growth never does.

This is all very fixable and I wish you luck in fixing it.

❤

Captain Awkward

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