Your most interesting date

Meaning one that really stands out in your mind as unique to your normal experience. This could be a single night date or a weekend that really had your mind spinning.

This could be a date with a new lover or even your SO/husband/wife. (This can apply to any type of relationship.)

There was this one weekend while dating a guy…it was a long distance relationship as he lived four hours from me. We met at my dad’s cabin outside of Breckenridge. The whole weekend we just played, almost like kids. We went hiking on Loveland Pass, we just sat there after a while, not saying a word admiring the valley. Later on that day we went for a hike behind the cabin and ended up having a serious makeout session on a trail. We probably would have ended up making love on the trail but for some reason we didn’t. We did later that night though. With the fire lit and some music on.

We also had dinner at a pasta bar where we were both introduced to Big Head Todd and the Monsters. Good tunes.

We drank Molson at a bar with a terrace (no longer there) on Maggie Pond at the base of Peak 9 with the September sun beating down and the sun reflecting off the pond. It was a nice romantic place at the time.

It was probably my most memorable weekend date.

I don’t usually date very imaginative men but this was a weekend that I treasure because it was all about us. Most men I date think that dinner at Olive Garden and hours of sex is a romantic date. While it can be, that whole thing gets old after a while.

Don’t be too explicit in this thread though. Be imaginative in your description if it involved serious love making or just plain mad passionate hot sex with little attachment.

< hears the sound of the big lead balloon dropping. >


It’s not the actual dates that stand out in my memory, it’s trying to get them.

There was the time I asked out the receptionist where I used to work and wound up watching a complete stranger get a dolphin tattooed on his ankle, but it wasn’t really a date.

Well, I’ve had some dates that I’m sure would be interesting to a promoter of abstinence education. They could write a textbook on How to Avoid the Possibility of Sexual Intercourse, based on some of the data I’ve amassed.

I dated a girl in my late teens, and EVERY date was awesome.

We used to do such inane things…Get in the car and ride around listening to the radio…Go to the airport and watch the planes land (At the end of the runway of course, much like Wayne’s World)…We found this spot off of I-95 in Richmond, Va with a little creek, surrounded by woods, and would just sit there for hours…

The list goes on.

Not that I was cheap mind you, we did all of the other typical “date” activities too, but those moments spent just wasting time are something I’ll always remember.

I would give anything to find someone who I liked being with, (and who liked being with me) that much again.

The most interesting date, huh?

Although I can’t really call it a “date” so much as a strange “encounter” it’d have to be 1988, a weekend around the end of June. I was living in Portland, Maine at the time. I had gone to a little pub called “Three Dollar Deweys” with some friends and a number of them had taken off early for various reasons.

I was more than mildly inebriated and toward closing time, a young lady walked up to me who I had seen in the pub a few hours earlier. She asked if I’d like to go home with her. In my state, I said yes for some reason (I should mention at this stage that I’m actually gay and hadn’t “been” with a woman at that time for a good 10 or 11 years) and we proceeded to head for her car, since I was in no condition to drive.

We never made it out of the parking lot and steamed up her windows in the process… She eventually drove me to her apartment where after a little nap, we continued what we had started in the car.

At any rate, the next morning, she made a very nice breakfast and I stuck around helping her do dishes and pick up the apartment until about noon.

Then, as I was leaving, she said goodbye (I hadn’t figured out how to tell her that I wasn’t interested in continuing anything with her) and she shocked ME by telling me that she wasn’t interested in continuing anything with me because she was actually a practicing lesbian - she said she got a little drunk and had a “man moment.”

After that, we had a terrific laugh as I told here about my status and we actually remained pretty good friends for the next few years until I moved away and we lost touch. She did introduce me to my next boyfriend, however, so it was a good thing.

A first date in Temagami.

The first night, paddling out across Wolf Lake, underneath a full moon and the northern lights.

The first day, swimming and diving at Paradise Pool. A small, cliff ringed lagoon with bottomless visibility, a waterfall for climbing and diving and swimming underneath, and a rock small platform for sunning, surrounded by the sweet scent of ferns and cedars.

The second day, paddling down the Temagami River’s Island Falls section, flowing with the water, catching eddies, surfing waves, dropping over the falls.

That night, a self-made sauna on a large shelf about ten feet above the turquoise waters of Wolf Lake. Glowing coals, hot steam, Karen and I whipping each other’s backs with birch slender birch branches, then running and diving into the cool lake, and floating on our backs looking up at the moon and stars. Then back into the sauna for another go-round.

My most interesting date took me for a late-night picnic at National Cemetery.
Nothing morbid, really. We walked around and he discussed the various battles that some of the soldiers fought in and we looked for unusual names. It must have been around Memorial Day because the whole cemetery was filled with flags placed by local boy scouts.
He even talked about the trees and flowers planted here and there.
It was quite nice. :slight_smile:

My most MEMORABLE date was not my BEST one. It was my weirdest. It was almost a year ago, in fact.

I had just started college and I went out with this senior I’d just met. We went to a Mexican restaurant, where he proceeded to tell me about his 15 sexual partners that he’d had, how they liked to have sex, things about their bodies…

I tried to be nice but he was getting WAY TMI. He was already on the Never-Date-Seriously list when he uttered the following line:

“What do you think about felons?”

I was flabbergasted. He then told me that his first arrest had been for indecent exposure, but the second was for stealing thousands of dollars of equipment from his former high school, and he didn’t regret it and would do it over again.

Needless to say, that date ended early.

I once spent the evening with a very funny, very attractive Northern Irish girl (for some reason they were all Northern Irish. Or Scottish) I’d met the previous weekend in a club. It was a great evening, marred only by her utterly terrifying devotion to Celine Dion. There was no follow-up encounter.

hehe, diggin’ these stories folks, keep ‘em comin’.

My favorite date is:
[ul]March 23, 1956[/ul]

As soon as I have a date, I will put it here. (It will have to be my most interesting date if it is my only one. :))

Nocturne - :slight_smile: Well, can’t deduct points for him not being upfront and honest. Better than finding out months into the relationship.

My most interesting date? Hmmm…That would be the one involving Cute German Girl, May 1997. Or, actually, the entire sequence of dates involving Cute German Girl. Dare I spill my guts on this one? Hmmm…this may take a while, and may be only interesting to me. Eh, frig it…Here it goes.

I don’t remember the exact date, but sometime in April, Cute German Girl walked into Cafe Express, where I had been working for several years as a barista to help pay the bills at Northwestern. I had just gotten off a semi-failed attempt at a relationship and gotten on a mild prescription of Prozac. For the first few weeks, I misapprehended her nationality and referred to her as “the Cute Swedish Girl.” (Compounded by an American prejudice I had at the time that somebody German couldn’t possibly be that cute. I’ve become much more worldly since then.)

We’ll gloss over the descriptions and fast forward. Needless to say, I became slowly enamoured. The accent. The freckles. The blond hair. The smile. The infectious optimism. And, well, the tits.

Next time Cute German Girl popped by, she had a stroller with her (baby included.) Aw, fuck, ain’t that just my luck. James Iha, of Smashing Pumpkins fame, happened to be in the cafe and opened the door for her. I took her order, she sat down, just another normal day at the cafe. Eddie, a former cafe worker and bassist for Poi Dog Pondering comes in, so we chat, he informs me that James Iha is sitting in the corner. Cute German Girl overhears. After Eddie leaves, I get my first break. CGG is a huge Pumpkins fan and comes to talk to me. I finally ask her name and about the kid. Her name is Nadine and she’s an au pair. Phew. Maybe there is a God.

Of course, I don’t work up the balls to have a full-on conversation to her until several weeks after that.

One day I decide “this is it. If Nadine comes in, I gotta be a man, get her number, ask her out. Gotta do it. I can do it.” After a few more Nike-inspired inner monologues, it happened. She came into the cafe. By this point, my co-workers knew my plan.

So I simply serve her with a friendly non-chalance, make small talk, and send her off on her merry way – to the middle room. OK, I’ve bought myself ten or fifteen minutes. What’s my line? Shit! How do guys do this? How do I hit on her without seeming like a slimeball? Arghh!! I do a round of washing the tables and ignore her. This is it. “I’m taking my break,” I announce to the staff. Oddly enough, I felt as though I had just said “I’m going out to get run over by a bus, could you get that last latte for me?” After all these days of working up my nerve and preparation, what’s my big line?

“Um…hi…do you mind if I sit here and talk to you?” Dude, it’s okay. Chicks kinda dig that cute nervous guy schtick. “Sure.” And we were off. About 20 minutes into our conversation, I had realized I never actually introduced myself. “By the way, I’m Pete. Can I show you around Chicago some time?” “Sure, here’s my number.” [cue 1812 Overture]

The first date is a flurry of activities. We start at the B’hai Temple in Wilmette, then catch part of a Northwestern baseball game. Turns out Nadine played baseball in Germany, and is a huge fan. Well, that’s easy. Next we go to the batting cages, where I embarass myself by whiffing on all ten pitches. This used to be easy. We’re getting hungry. Turns out she’s a vegetarian (somehow, I end up with a disproportionate amount of veggie girlfriends.) Turns out she’s unfamiliar with Indian food. Devon Avenue it is! Samosas and vindaloos and lassis all around! Yippee! Man, this girl is so cool. Shall we keep this night going? I pick up the check, and ask her whether she’s getting tired, or would like to hang out some more. She wants to hang out. You da man!.

We drive down Lake Shore Drive to Taylor Street, get some Mario’s lemonade, and then I take her to the Sears Tower. OK, you gotta slow down here. Don’t want to show her all of Chicago in one night. Finally, I take her home. First date, I generally don’t kiss. Besides, I don’t know whether this is a date date, or just a date, so I peck her on the cheek goodnight.

I light up a smoke, open the window, crank up XRT and enjoy the high all the way back to Evanston. It’s either the Prozac or Nadine, but damn something’s working.

Next few weeks, I’m the proverbial boy in love. I ditch my Prozac prescription. Life is good. Really good. But I still haven’t kissed my fine fraeulein. She’s very comfortable with close physical contact, but gets all weirded out when I try to kiss her. Something’s up here. I know my breath doesn’t stink, what’s the deal?

During our next date, I invite her over to watch movies. Perhaps Wallace and Grommit and Ferris Bueller’s Day Off aren’t movies to rent when you want to get laid, but these were the perfect movies for us. I picked her up. She wore a very provocative, low cut dress, and a blouse that accentuated her finer points, so to speak. We get on the counch, watch the movies (after kicking my roommate out), and basically end up in a spooning position. All signs read “go.” I kiss her neck and ear, and receive encouraging groans. I lay my hand on her breast. She doesn’t swat it away. She doesn’t shudder. OK, so far so good. I move in for the kiss and she turns her head. I have gotten to the breast-fondling stage without passing through the kissing stage. Huh? That’s a ground-rule double for you folks keeping score at home. Well, this definitely isn’t in the troubleshooting section of the manual. I’ve seen this on Pretty Woman, but I don’t think Nadine is a hooker.

Maybe she’ll be more comfortable in the bedroom. (In retrospect, perhaps not the soundest line of thought.) She agrees to come into the bedroom. I’m still befuddled. She has no problem with me touching her. As I later discover, she has no problem with me touching her anywhere. In fact, she rather seems to like it. As soon as I realized I was, in effect, “rounding third without having stepped on first,” I decided this was way too weird for me. I know Europeans are a bit different, but I’m sure this can’t be chalked up to a cultural difference.

One last ditch effort. I lay on top of her and slowly go for her lips. I notice her tense up again and quiver. OK. This stops right now; something is way wrong. Somehow, I manage to put the brakes on my raging hormones. All systems shut down. Time to have a talk.

The problem? Turns out she’s still carrying a torch for some guy she broke up with two years back. But then, she mentions some other guy since then whom she lost her virginity to. “Um, did you kiss that guy?” Silence. It’s obvious she did. Argh! She seemed so normal. (Actually, she did turn out to be quite normal in the end.) I’m thrust into wondering, like a 13-year-old schoolboy, does she really like me, or doesn’t she? There’s no reason she shouldn’t, yet none of this makes any sense to me.

We finish talking and I drive her home.
There’s more to all this, but this has already gone long enough, and it’s a truncated version. I do win the girl in the end, at least for a time, and do get that kiss. But there was still about two months of preparatory work ahead of me.

My friend set me up on the date from hell which was interesting in a “watching a car crash” kind of way.

The girl was a vegan (my friend neglected this tidbit of info) and I took her to a French restaurant. Ever try finding something suitable for a Vegan at a French restaurant? Herding cats is, I believe, slightly easier. She ended up with French Onion Soup, a side salad and a glass of water. Seeing the impending train wreck coming I went for several very large martinis, a bottle of wine, tiger prawns and a beautifully cooked steak with mushroom sauce. If looks could kill I’d be staring up at you all from hell.

She was a far, far left wing trade unionists daughter (bordering on communist) vehemently opposed to pretty much everything I believe in. An entire evening of 2 sentence conversations desperately trying to find even the slightest common ground between us.

I still shudder at that date, but at least my “friend” was highly amused.

Most eminently wonderful date would probably have to be that time I took the two gorgeous gay Esperantists from Florida out dancing and then spent the night with both of them. Unbelievablyamazinggreat.

My parents were in Cuba, even, so I got to use their house and didn’t even have to clean up my apartment.

Oh dear- most french onion soup contains beef broth…

That’s what I was thinking…And cheese…definitely not vegan. But I’m sure she noticed the cheese.

When I started dating after my divorce I had no idea how to meet people so I resorted to a medium I felt I knew fairly well–the Internet. I placed a personal ad and let the replies roll in. I met quite a few very nice, stable and interesting men–one of whom is now my SO. Of course, I did have a few memorable experiences, too…

Mark and I emailed for a couple of weeks before we actually met for lunch at a local restaurant. He claimed to be 39 (I was 33 at the time so that seemed like a good match), tall, and “ruggedly handsome”. Needless to say I was rather surprised by the man who met me–well, he was right about being tall, but if he was really 39 then the years had been kicking him in the face on a fairly regular basis. Now don’t get me wrong, I’m not picky about age or looks, intelligent and funny are far more important to me, but I don’t like being lied to–and I had been as I was to find out.

Well, we got down to lunch and Mark seemed just as nice in person as he had in our correspondence–until he mentioned his wife. “Excuse me?!” I managed to choke out. “Oh, it’s okay,” he assured me, “we have a very open relationship.” But as I dug deeper I found out that he was really the only one of them who knew they had an open relationship. “But she doesn’t understand me,” was his explanation. “That makes two of us!” I told him. And, since I couldn’t help but ask, “the thing about being 39–that was a bit of a fib, too, wasn’t it?” He smiled and said that yes, he’s really 54 but he feels 39. And I smiled right back at him and told him that he wouldn’t be feeling 33 any time soon–but thanks for lunch. :slight_smile:

Well, this was certainly memorable, if not in a good way.