Tales of The Sexually Unsuccessful

Anybody who can relate to the first 11 seconds of this clip from Trainspotting <– possibly NSFW will understand the thrust of this thread.

Bring on your tales of nights when you were invisible. Expound upon the joys of obliviously shooing away a person who you want to attract.

Clueless of the world unite and commiserate!

In high school I had a crush on Debbie (not real name.) For months I mooned over her, thought about her, fantasized about her. In fact I did everything but talk to her.

Close to the end of the year we got on the bus together and despite the number of empty seats she sat next to me.

Debbie starts in about how Peter O’ Toole is her favourite actor and how much I remind her of him.

Me: [internally] She’s comparing me to a drunk, womanizing notorious asshole.
Me [Verbally] But I’m nothing like him.
D: Oh yes you are and I think he is the coolest person ever.
Me: No, really, I’m nothing at all like that.

This went on for the whole 20 minutes of the bus ride. Finally we reached our destination and went our separate ways.

Two months later I was taking a piss when the scene flashed through my head unbidden and a very loud and annoyed voice in my head yelled, “She was trying to pick you up asshole!”

Observation skills such as these in combination with my scintillating and welcoming personality are likely why I was a virgin until 21 and the next best thing till I was 24.

As the shy, short nerd, I had my issues with talking with girls in HS, but what you described is in a whole 'nother league of dumb.

Wait, am I supposed to be supportive in these kinds of threads?

I wish I had something to post.

Gotta admit, you have a point.

Rico Suave was I

I have since spoken to her a couple of times; I dodged a bullet.

That doesn’t mitigate or excuse the fog of oblivion I was in that [del]day[/del] decade.

But hey man, no one ever hits on me - I didn’t know how to recognize it.

(Zeke slinks into the corner and hides his face)

Don’t be too hard on yourself, she wasn’t trying hard enough. Girls need to stop thinking that guys pick up on hints, we’re not wired that way. Heck, I was always so utterly oblivious to signals from the fair sex that a girl would literally have to get into bed with me naked and grab my junk before it would dawn on me that she might actually like me a little bit.

Naw, not too hard on myself. Just a little chuckle at an insecure and naïve whiff at a perfectly thrown ball.

I just want to hear similar stories so we can laugh at each other as well as ourselves.’

Here’s another one. Incredibly hot sister of a friend of mine is at a house party with me. We start talking and she mentions she’s bored but doesn’t know what she wants to do. Joking I said,
“Well, you could blow me.”
She said, “okay” took me by the hand and started leading me to the shed. I chickened out about halfway there because “beautiful women don’t agree to blow me at the merest suggestion. This must be a set-up.” So I turned around saying something like, “hahaha good one.”

I went and got a beer and sat down and about 15 minutes later - after she got done blowing some other guy - she sat down beside me and said, “I was serious. All you had to do was follow me.”


The way it always seemed to me was: if a girl was with a guy, she was taken, if she was with a girl, she was taken and a lesbian, and if she was alone, she didn’t want to be bothered.


Couldn’t have put it better myself except to finish the sentence,

“…she didn’t want to be bothered - by me.”

I missed every sign of interest from girls throughout my 20s, because I was so oblivious (and shy). It wasn’t until my early 30s that I started having real relationships.

I had a female friend literally ask me, repeatedly: “So, are we going to have sex soon, or what?” Well, we eventually did… eleven years later. That’s how long it took before the light bulb went off over my head.

Interestingly, she got settled into to a long-term and very adult relationship with someone else immediately after that. I know it’s probably a coincidence, and that I shouldn’t flatter myself, but I do wonder a little bit if she didn’t want do that without doing me first. I bet she breathed a sigh of relief when we finally got it over with…

(BTW, the actual sex was - and we both agree on this - utterly and completely terrible.)

I’ve told this one before, but it seems to fit this thread.

I started working at a new company, and had moved across the country to do it, so I didn’t know a soul. After a while, I was seriously crushing on a coworker. And we had gotten to know each other a bit; went to lunch once or twice. Now, I had a history of my own signals not being picked up (or not making myself clear enough, depending on your perspective), so I decided I had to do something unmistakable. So I gave her flowers on Valentine’s Day and invited her to a play the following week. She said yes, hooray.

A couple days later she sent me an e-mail asking if I could get an extra ticket so she could bring a date.

A great opportunity for a threesome. :wink:

(Hey, what can I say, I’m an optimist.)

A relevant quote comes from The 40-Year-Old Virgin:

“I like women. I respect women. I respect them so much I completely stay away from them.”

That was me. Same as others here, the idea that a woman might hit on me was unfathomable. I really should have worked on my confidence more when I was young.

Two memorable examples:

  1. I was exiting a parking lot, allowing this really cute girl walking on the sidewalk to pass by my car. Looked nice, not trashy or life-on-the-street or anything. She turned and looked at me, catching me watching her. I smiled awkwardly, and she smiled back. She came over to my window and asked if I was going down (whatever the street in front of us was) past (some other street), and could I give her a ride if so.

Obvious correct answer: “Why yes, I am!”
Answer I gave: “Uh, well, no, I’m going the other way.” Which I was, but still.

  1. In the early days of the popular internet, I struck up a private-message chat with a likable recently-divorced woman of average, entirely reasonable appearance (we exchanged photos). After a chatting every couple or few days for a week or two, our exchanges started to include some sexual content, all coming from her. She sent a picture of her bare back to show me her tattoo. On a Monday when I asked what she’d done the previous weekend, she hesitated and then fessed up “Got laid”- she’d traveled to have a dalliance, her first since the divorce, with a guy she’d met online. She sent “funny” explicit porn pictures (photos from some magazine with models dressed as Bill Clinton and Monica doing sex things). She engaged in some mild flirty talk, then said she would have stopped but her nipples were poking hard through her shirt so she decided to keep teasing me. Even with this, I did not catch on that she was trying to have (at least) sex chat with me.

Now, maybe either one of these women were trying to use sexual allure toward me with malicious intent, and I was only saved by my cluelessness. Following up on either of them may have been a bad idea. For this thread, it doesn’t matter- the point is, I completely failed to see even these absurdly obvious come-ons. To this day I’m astounded at my own obliviousness back then.

Ouch man that hurts - obliviousness finally rewarded by tedium or worse. Hats off my friend; hats off.

Man, that’s entirely brutal.

Wow. That’s so cool, it’s like we could be brothers… or the same guy.

At 12 I was crushing on this grinning, dark skinned kid with blond curls who hung out at the swimming pool all summer. Caught him standing in a group of some of our mutual friends beside the deep end and gave him a flirty, playful shove on my way to the diving board.

He damn near drowned. His best friend knew he couldn’t swim and jumped in and saved him while I stood there dumbfounded. He was terrified and embarrassed by the incident and barely spoke to me for years even though we attended the same high school. I never got over my crush or my shame.

So when he looked me up on Facebook 25 years later and saw some pics of my kayaks, he asked if he could go paddling with me sometime. Still nursing that crush and hoping to make it up to him, I volunteered to take him down the river with me and assured him that I’d supply the PFD’s and other safety stuff. You know. Because he doesn’t swim. Another strikeout, shouldn’t have brought it up. He replied with “Hey, hey, hey… I learned to swim right after some chick tried to drown me when we were kids.” He seemed pretty comfortable in the kayak, so I took him over a class 3 or 4 dam thinking it would be a pretty simple maneuver. It was rough going, even for me, and I’ve been paddling more than half my life. We made it over safely, but in the churning froth below the dam we both dumped our boats and watched our beer float away while we scrambled to grab paddles and other essentials. We spent the rest of the trip soggy and thirsty.

But I guess it’s never too late to make good on a romantic fumble. We eloped a couple months after we floated the river. He still tells everyone I tried to drown him. Twice.

Wait a minute, guys say women shouldn’t hint, just be blunt… which does that count as? :stuck_out_tongue:

I acknowledge that I am an extreme case: Usually, as I said, only a direct physical assault is blunt enough to make me get the picture. :stuck_out_tongue:

I basically figured she wasn’t serious. People say a lot of stuff without meaning, it, right? And why would she like me, anyway? Etc.


Actually, and sorry about double posting, but I should expand slightly on how it finally went down, just to illustrate the problem.

So what actually happens after eleven years of this is that we’re at a bar with a group of friends, and we haven’t seen each other for a long time, and she’s recently single, and I’m all worried over some imaginary problem or other that I can’t remember now.

So she starts rubbing my back. And I figure, well, she’s trying to comfort me, that’s nice.

Then before long, we’re all snuggled up, and I’m thinking, well, this is nice, I can enjoy a snuggle between friends.

Then everybody gets up to leave to go to some party. I decide to go home, because I’m boring like that, and she says, “Hey, I don’t feel like going to that party either, how about we both go back to your place instead?” And I say, “Oh, come on, wouldn’t you rather be at the party? My place is no fun.”

And she says, “No, I *really *want to go back to your place.” And I say, “No, come on, you’ll be much happier at the party.”

So she says, “I’m serious, buster, we’re going back to your place.” And I’m thinking, well, this is weird. I hope I have some movies that she hasn’t seen that we can watch, or something.

So we get back to my place, which is just a small one-room apartment, so the bed is the obvious place to hang out. So, we’re in bed, talking for a little while. And then at some point we get under the covers.

And then I’m thinking, “Hang on, why is she taking her clothes off?”

Also: “Why is she kissing me?”

And *then *I get the idea.

I’ve already posted my collection of stories of my own epic cluelessness at reading “signals” from women.

I do a routine in my stand up about women complaining that there are no nice guys out there. The reality is that there are LOADS of them but women don’t want to date them. They just want to be friends. They want to date the “bad boys” and the change them into what they really think they want which is a nice guy, when they could have dated a nice guy in the first place.

Oh, the women find this much funnier than the men because there is a lot of truth to it.