Worst/best first dates you ever had?

submitted by PasLagardere from self.Lesbians

As the title says, what are the worst and/or best dates you ever had?

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[–]xv_xx 7 insightful - 5 fun7 insightful - 4 fun8 insightful - 5 fun -  (2 children)

Not the worst, but definitely one for my "gallery of horrors", was one time I went out with this girl I had just met. We went out for drinks, got animated, and went back to her place. She was very intense, and somewhat dominant, which was properly turning me on. So, we were in bed, already half naked, and she tells me to wait a moment, she was going to go for "something fun". She went into the bathroom and closed the door behind her. I'm not sure if she was gone for just two minutes or 15, I was in a bit of a weird place, turned on and wanting to keep going, so I was more than a bit impatient. BUT, I was also getting a bit of anxiety -- I had never moved so fast from meeting someone to having sex with her. And she was taking forever, which wasn't helping. And then, after what felt like forever, she comes out of the bathroom wearing a massive strap-on and nothing else. It was like 12 inches long and, er, anatomically correct: flesh colored, veins, the whole shebang. You have to know, at this point in my life I had never ever had sex with a strap on, and the only time I had even seen a real erect penis in my life was a) much smaller than that dildo, and b) not an experience I had fond memories from. So, when I saw her standing there with this thing on I lost it and started laughing hysterically and uncontrollably. Like, I wanted to stop laughing but couldn't. Mood was not so much killed as obliterated, she got very annoyed at me, the whole thing was a complete cringe-fest.

[–]SailorMoon2020 3 insightful - 1 fun3 insightful - 0 fun4 insightful - 1 fun -  (1 child)

I remember you said this on True Lesbians. I didn't have an account so I couldn't ask then. It seems she had herself a strap on fetish. Well, did y'all still do it once the laughing subsided?

[–]xv_xx 4 insightful - 1 fun4 insightful - 0 fun5 insightful - 1 fun -  (0 children)

I did! Ah, the good ol' days of TL... I don't have an issue with strapons nowadays, I actually love using one with my gf (both me using it on her and vice versa). But back then I was just too inexperienced. I knew what a starpon was, and I _was_curious, definitely. BUT, this was a first night out and there was absolutely no prior discussion or even hinting at using a strapon at all. If it had been someone I had been dating for a while and had had conversations about it before (as it eventually happened with a different girlfriend) then it might have gone differently. But she just came out with it expecting me to just smile and take it, and I was just not going to do that. I mean, it wasn't even as if she had walked out of the bathroom with the thing in her hands and asked if I wanted to try it, she just went all in (metaphorically speaking). So no, we didn't do it. I just got dressed, made some excuses and left. I met her a few times after that (we had friends in common) and yeah, it didn't really work out. She wasn't even cool about it, like I tried to make a joke to lighten up the mood, but she just gave me a weird, offended look. People can be weird sometimes.

[–][deleted] 5 insightful - 1 fun5 insightful - 0 fun6 insightful - 1 fun -  (0 children)

Worst: This girl showed up super late, spent like 20 minutes in the bathroom, and gave single-word answers to most attempts at making conversation. At the end, she suddenly seemed weirdly into me and guilt-tripped me into letting me put her number in my phone. I never called or texted.

Best: We met for drinks at a history-themed pub, then I took her on a walk around the neighborhood because she was new in town and hadn't been around there yet. We were eating dessert from one of the shops outside when a big fluffy dog ran away from his people and came up to us wanting to be petted. Conversation and physical chemistry were good, and we ended up dating for a few months. The only thing that went wrong that evening was a random man attempting to hit on us both...

[–]SailorMoon2020 3 insightful - 2 fun3 insightful - 1 fun4 insightful - 2 fun -  (6 children)

The best date I went on is nsfw.

The worst...well, it wasnt that bad, but was kind of, 'wtf', was when I was in Germany. I met up with a woman and went back to her apartment. She told me to not go in one specific room and I shrugged it off, and said 'okay'.

After we did what we did, I was hungry and she offered to make me something. As she was fixing something, I went to use the restroom. Nude, naked. Butt nekkid.

I came out the restroom and heard a, 'Oaaahhhhhaah ughhh ahahhh' like cough. It was coming from the room. I went to the room and the door was open, and all was there was darkness.

Then from the darkness, crept an old frail woman. Hicking, and hacking toward me with a walker with wheels and not tennis balls.

The woman came from the kitchen and ushered her grandma back into the room.

To this day, I don't understand why she was taking care of grandmama and not her mom.

[–]piylot 2 insightful - 2 fun2 insightful - 1 fun3 insightful - 2 fun -  (5 children)

The best dates are often nsfw and we'd love to hear about it

[–]SailorMoon2020 1 insightful - 1 fun1 insightful - 0 fun2 insightful - 1 fun -  (4 children)

Lol, what kind of woman would I be if I told all and left none?

[–]piylot 3 insightful - 4 fun3 insightful - 3 fun4 insightful - 4 fun -  (3 children)

The kind we need to spice up the forum

[–]SailorMoon2020 2 insightful - 1 fun2 insightful - 0 fun3 insightful - 1 fun -  (2 children)

Nej! Because if we do then the thread would turn to NSFW and since most people have that filter off, they won't see nor respond to the thread.

Also...

I'm on the first day of my period so I'm ugh, right now. However, tomorrow I'm up for it. =D

Hey, Piylot. Does anyone else get really horny while on their periods?

[–]piylot 2 insightful - 1 fun2 insightful - 0 fun3 insightful - 1 fun -  (1 child)

For me mostly the days approaching it but sometimes also during

[–]SailorMoon2020 1 insightful - 1 fun1 insightful - 0 fun2 insightful - 1 fun -  (0 children)

Hmm, for me, it's during and after. However, about five or scene days prior to my cycle, I'm not aroused at all.

[–]piylot 2 insightful - 1 fun2 insightful - 0 fun3 insightful - 1 fun -  (0 children)

Worst - struggled to make conversation. Found out halfway through she thought I'd asked her to hang as friends. She was actually gay and interested just didn't realise I was too. Got better after that though.

Best – Good flow of conversation, left the bar after a couple of hours to go back to hers and the chemistry was good. Got worse after that.

I've never had such a bad first date really because I go in with low expectations, it's a lot to spend hours with a stranger and hope there'll be mutual interest and no awkward moments. I've had plenty of bad second dates, that's when the expectations creep up a little

[–]chupacabrawitch 2 insightful - 1 fun2 insightful - 0 fun3 insightful - 1 fun -  (0 children)

The best one was when i met my wife :)

The worst one actually didn't start off too bad and was going pretty well, met up for coffee then took a stroll around town during an art festival. Then she casually dropped that she had a boyfriend and that they were trying out dating other people separately. Which is fine, if all parties were knowing and ok with it, but I totally did not know as she did not bring it up beforehand and did not indicate in her dating profile whatsoever that she had a partner already. So that was a deal breaker and crushed me a little...not here to be a "third"