It probably wasn't technically a 'date', but oh man, have I got a story for you...
Prepare yourselves for the tale of how I was almost in a porno once.
So, I'm living in Southern California (and loving it) at the time, having moved out there after high school from a small east-coast town that could best be described as 'alcoholism and meh'. I'd only been out there for maybe 2-3 months, but a friend of mine - really more friends-with-benefits than friends - decided she'd take me up on my offer to come visit over spring break.
Now, I quite liked this girl... Or at least, I think I did. 19 was a weird age for me, what can I say. The problem was, our 'relationship' was always pretty messed up - I've more than my fair share of psychological issues and she might as well have had the words 'damaged goods' tattooed on her forehead. As a result, I was never really sure how to treat her, as sometimes she would behave like the very idea of sex offended her deeply and other times (that is, EVERYTIME she'd had more than 2 drinks) she'd jump almost any bone that appealed to her in that moment.... That's mostly irrelevant to the story at hand though.
So, she decides to come spend 2 weeks with me, and I agree. Despite the fact that I don't do well living with others, being something of a loner. Let's just say it was a very strange 2 weeks.
Easily the most note-worthy event therein however, was meeting a 'family friend' of hers that just so happened to live in the area. Apparently this woman, who I'll call R, was likely in her early 40's, used to work for my friend's father and that's how they knew each other; but, since then, she had met a wealthy west-coast gentleman and decided to start a relationship which soon led to their being engaged (ie, she had decided that doing nothing seemed preferable to having a job, and was willing to marry/bang this wealthy overweight man if it meant she got to live in a nice house and not work). As I didn't know many people/places in the area yet, we decided to go hang out with this woman for awhile.
At the time, I didn't find it overly suspicious when R offered that I just hang out at her house while she and my friend went for a drive, though I still rejected the offer and went with them - and I'm glad I did. It was during this drive around town, taking in the sites, that I got the first inklings that something wasn't quite right - R kept bringing up very sexual topics, asking strange questions of myself and my friend, and generally behaving rather strangely for a 40 y/o woman hanging out with two 18 year olds.
Again, at the time, it didn't seem overly suspicious - I figured she was just kind of a weird older woman. She offered we come by the next day to travel down to San Diego, and we agreed.
The next day, my friend and I arrived at R's place and let her drive us down to San Diego. At the time, I didn't find it overly suspicious that R brought us to a huge mall - though it quickly began to arouse my suspicions when I realized R was bringing my friend into all the most expensive stores and showing her things (mostly clothes) that cost thousands of dollars. And that she kept asking my friend things like 'wouldn't it be lovely to have this?", "dont you wish you could afford this kind of stuff?" and "this would look great on you - wouldnt it be nice if someone bought it for you?".
Whatever, I thought as we left the mall, it must be a woman thing. Oh, how wrong I was.
So, next up, R asks if we'd like to go to a party at her friend's house, which we agreed to, seeing as she was driving and we had nothing better to do.
Again, my suspicions are aroused when I realize her 'friend' lives in an area of the city (I want to say it was called Hillcrest) known as a hub for homo/transsexuals and sex workers.
My suspicions are aroused further when, upon entering R's friend's home, we find that he is in fact in his mid-20's and supposedly a friend of R's step-son.
And the only furniture in his front room - of a very nice house I might add - is a large leather couch.
Across the room from the couch, three video cameras on tripods sit, pointed directly at the couch.
On the couch, a very nervous looking - yet very attractive - young woman sits, looking thoroughly disheveled (hair and clothes a mess, eyes slightly watery, gripping her purse nervously before her).
Immediately, my 'this is a porn set' alarm starts going off; though, my friend seems none the wiser, and happily accepts a beer from our host. The disheveled girl quickly leaves upon our arrival, whereupon I realize that the only people at this supposed party are the host and one of his friends. When I mention this, the host seems utterly perplexed that there was to be a party, to which R quickly stammers something about him saying there was a party tonight and he responds by picking up the phone and calling people.
Its at this point that R says she's going to head home, but that we should feel free to stay and enjoy the party. It was suspicious in itself, but the vehemence was really telling - she was saying whatever she had to to ensure we stayed at this house, eventually saying she would come back later in the evening to take us home. My friend seemed to be having a decent time, so I agreed. Things quickly headed downhill from there.
A stream of dudes soon began to appear, all in-shape and wearing expensive designer clothes, at least 10 in all. I see my friend sitting on the leather couch with our host, who is behaving in a most skeevy manner (trying to put his arm around her, pretending to know massage in an attempt to feel her up, offering to buy her several $700 designer shirts like the one he was wearing) - but, as my friend wasn't outright complaining, I figured she was having a good time.
She must have gotten nervous when some of the guys started setting up the cameras in different areas (all focused on her on the couch) though, because she came to find me in the kitchen - where I had just finished a conversation in which two of the dudes told me a I was 'really well built' and 'very handsome' - to ask if we could get the hell out of there. I agreed, but my phone barely worked due to dying battery and I didn't know many people anyway (having only lived in the area a few months). Luckily, one of the few friends I did have - dude, Cody, THANK YOU FOR BEING THERE BRO - answered and, after laughing hysterically, agreed to come pick us up.
What followed was the most skeevy, pathetic, downright-disgusting series of events I've ever been involved in: the minute the assembled group of dudes realized we had arranged a get-away, they began to do everything in their power (short of using force - though there were threats and it did seem that was a possible outcome a few times) to separate me and my friend and get her alone with our host, who seemed to be running the show. They tried to lure her into a back bedroom and lock the door, but she was having none of it. They tried to convince me to wander off with some of the guys down to 7-11 just down the road (which I realized upon leaving didn't actually exist), but I - not to mention my friend - wasn't planning to let her out of my sight. It only made this more vile when, in a slightly-drunken moment of arrogance, the host began to tell us about how he met R through his friend (R's step-son) - and how she was a total whore that routinely had group sex with the host and several of his friends, including her own step-son.
When buddy arrived to pick us up, they gave up on the lies and became very blatant, offering my female friend an all-expenses-paid shopping spree the next day if she would spend the night and offering my buddy (the driver) $200 to leave her/us both behind. Needless to say, neither accepted that offer, and we drove the hell outta there in a hurry.
It wasn't until later that my friend told me how the host was constantly trying to feel her up, whispering REALLY sexual things into her ear and making outrageous offers of money and goods if she would spend the night with him.
At this point, I was incredibly pissed off. My buddy drove us back to R's house, where my car and keys were still, at which point I kicked their front door several times, nearly taking it off the hinges. R's answered the door, and I pushed past her, indignant and shouting about her exploits (both with us and our earlier host)... I vaguely remember her husband being there during my shouting, which I believe I was hoping would get him to call off their engagement (for his own sake, mind you). I was quickly handed my keys and we then headed for home.
It was, without a doubt, the weirdest and most uncomfortable 'date' I've ever had, and generally skeeved me out.
I'm not so sure what my friend thought though... That night she wanted to watch porn with me.
And apparently she kept the host's number in her phone, because he called her the next day and she snuck into the bathroom to chat with him.
And I learned that, several years later, she returned to California - with her parents - to attend the wedding of R and her overweight husband.
She never told her parents that R tried to lure her into doing a porn, and there's reason to believe she contacted the host while out there.
Generally an unpleasant, if slightly hilarious, memory.