I suppose many people have a “one that got away” – a person you were interested in, or they showed interest in you, but for whatever reason, the two of you never gave it a go.

Let’s hope that you, unlike these 15 poor saps, don’t only have your own bad judgement to blame.

15. That party could have kept going.

Was a groomsmen at my best friends wedding. Just three groomsmen and three lovely bridesmaids. Had a ton of fun during the reception and with the groom, I got everyone out on the dance floor when dancing started. Really extroverted night cause I was just in a great mood.

Later standing around with the bridesmaids and one asked me what I was up to after the wedding. I was thrown off cause it was 9 and I was mentally like, “this is the nights event”. I ended up saying, “I dunno, probably go home.” To which she replied, “Oh, well I have a hotel room, dont mean to brag or anything…” And ‘jokingly’ talked about me being jealous. And then naturally I said, “Whoa, where did all this honey come from?!”

As I just discovered the gift bags with fresh honey. Was about 2 hours later when I was taking off my bowtie that I stood and stared ahead realizing my mistake…..MFW

14. Hahaha yeah good thing.

I was in an editing booth with a girl (who is now a runway model) in college. She suddenly bursts out with “I wish I was a sl*t, because it would be so much fun to f*ck in this booth.”

I just said “Good thing you are not a sl*t then.” and kept working.

13. There was no next time.

Went on a date with the most beautiful girl I ever went on a date with. It went really well. I had delved into her soul, really gotten her to open up, and made her laugh a lot.

I got her to talking about paintings she makes but has never showed anyone, and made her promise to show me some time. I walked her home, and then she was standing on the first step of her stairs, facing me at eye level, smiling. Somehow, suddenly, I felt self-conscious. I got nervous.

So instead of kissing her like she clearly wanted me to, I gave her hug, thanked her for the pleasant evening, and walked away. I felt amazing. The date was over and I hadn’t f*cked it up! A few minutes later, I got a text from her. I should have invited you up… to show you my paintings. And, for the love of f*cking god, I don’t know how I managed to send this as my reply: Haha, next time!

There was no next time.

12. I mean she did say she wanted to get out of there.

Let’s see if you can beat this one.

I’m out with three people. My best friend, his girlfriend, and a friends of hers. I’m completely oblivious that I got set up for a double date. The girl is beautiful. We get along. We end up at some party. It’s fun for a while, the girl is chatting me up, then we run out of things to say. Then we realize the couple left. I start to get uncomfortable. I don’t know anyone at this party.

After an awkward silence where we’re both looking around the room, she turns to me, looks me in the eye and says the magic words. “Let’s get out of here”. I happily oblige.

We walk down the stairs and into the street. “Alright, see you later” I say to her, and proceed to get out of there.

11. Finally, a happy ending.

Once upon a time I met a man at a reddit meet-up. I messaged him on Facebook and told him about a new restaurant by where I worked, ‘never heard of it’ they have really good and cheap Bloody Mary’s, ‘I don’t like mixed drinks’ oh, ok, ttyl.

Then I read a post on Reddit that was sooooo amazingly similar to this post and I realized he had no idea I was trying to ask him out for drinks.

So I contacted him again on Facebook, clarified that I was no longer in a relationship, and we set up 2 dates.

Got married in June.

10. That girl probably had a complex for awhile.

showed up at a girls place (she knew i was coming over, didnt know when) and she answered the door in bra and panties. I got what i needed to get and left.

i am an idiot

edit: no, “got what i needed to get” did not mean sex. I should have noticed that, but I didnt. =[

edit: she is also a redditor.

9. He was not just being friendly.

I was once blatently hit on by a gay guy for like 2 hours and when my friend and I left she looked at me and said “you know he was trying to get with you, right?” I had no idea. I thought he was just being friendly.

8. Third time wasn’t the charm.

Camping trip for a geology class.

I’m cold, can I get in your sleeping bag?
It’ll be warmer if you take off your damp clothes

ok, i took off my clothes, can I get in your sleeping bag now?
No, I mean it will be warmer in your sleeping bag.

oh. screw it. I’m going to sleep

7. Not a match made in heaven.

Once I spent an entire night with a girl that I really liked from school. It was 24th of July, Saint John’s day, which is celebrated with a big party in the streets of Barcelona.

Towards the end of the night we were talking and she said she wasn’t the kind of girl that made the first move, even when she really wanted to, due to her shyness.

My answer? “Yeah I’m also like that”.

It still eats me up a bit, I still really like her, but we went on separate ways…

6. Oblivious is an understatement.

I used to hang out with this really cool chick, she was into PC games and such, and we had similar music tastes. Our personalities are scarily similar, too. We even share the same birthday.

Anyways, I digress.

She was over at my house once, and we were the only ones there, both in my bedroom. She was wearing a short skirt. I was showing her something on the computer, I think, and she laid down on my bed… in a skirt… and implied that I should come sit.

Didn’t even realize she had done it until a couple of years ago when we were having a conversation and she told me that she used to have a major thing for me and cited that situation.

I was rather oblivious back then.


While I was in college, a girl that lived in a dorm 2 buildings down calls me up after just leaving my place and meeting me for the first time and says “So do you want to come see my cat?”

“WHAT?! You’re not allowed to have pets!!”

4. Doesn’t everyone know the code “slip into something more comfortable?”

In high school, a girl asked me for a ride home from a football game one time, to which I agreed. She asked if I wanted to come in and see her room (I forget why this seemed like a normal thing), and that it wouldn’t bother her parents because they weren’t home.

So, I went in and had a tour of her house. We both went to catholic schools, right down the street from each other (mine was all-boys, hers all-girls). Her school had the traditional catholic school uniform; plaid skirt, knee-high socks, and white shirts. So, when we get into the house and are in her living room, and she says something along the lines of “I think I’m going to get out of this uniform…” to which I replied with (roughly) “Oh, ok. I’ll just wait here till you’re finished”. I was pretty pissed off when I figured it out a while later.

3. You had to get up early, really?

Freshman year I was chatting up two girls at a party. During the course of this rather long conversation, one of them started playing a little bit with the other’s (quite large) chest. Not massaging or anything, mind you, just making them bounce and such. I’d met both of these girls before the party and one of them lived in my dorm, so it never occurred to me that they’d actually be flirting with me.

Towards the end of the evening, one of them looks at me and says, “Hey, GreatDayForGuinness, her roommate (gesturing towards the other girl) is gone for the weekend and I’m spending the night in her room. You should come too!”

I politely excused myself, citing the fact that I had to wake up early the next morning.

It took me longer than I care to admit to realize what I may have passed up on. Much regret has been had since.

2. Why couldn’t she just talk?

I was in a club being drunk and happy, when a cute girl comes up to me and hands me a note. She stands there while I try to read it, but can’t, because of my drunken state. I decide to pretend like I read it, and look at her, smile and give her the thumbs up. She looks at me like: “what’s your problem?” and walks away. The next morning I find the note and it reads: “you look cute, take me home”.

I hated myself for being so stupid, but when I was in the club, I just thought it was weird that some chick gave me a piece of paper. Didn’t even cross my mind that it was a proposition.

Btw, not gay

1. I guess that was her answer.

Laying on a bed with a girl I liked and her friend.

Her friend rubs my back and asks if there is anything I wanted to do.

I started playing Sonic 3.

I should have played Sonic 1.

These are killing me – I don’t know whether to feel worse for the girls or the guys?

Do you have someone like this in your past – a missed opportunity?

Tell us the story below!