Your Last First Date

July 20, 2012
Category: Dating

Drinks. Dinner. Transactional conversations of what you do, where you grew up, what you like, blah, yada, blah. If this sounds like your typical first date, you're not alone. Maybe it's just me, but it feels like first dates have gotten stale. Whether it's from playing it safe or trying to keep your enthusiasm in check, it seems that these days most first dates just go through the motions. Don't get me wrong, drinks are always a safe and trusted first outing for getting to know someone. This is especially true when the date is going nowhere and you're able to excuse yourself after the second round. But all too often these dates can feel scripted and stale. Which is why I'm putting an initiative out there to start getting creative with first dates and start making them more of an experience. Some of the greatest dates I've been on are ones that are active, adventurous, and best of all unpredictable. If you're the planner, there may be some hesitation in putting effort into a first date (oh the games we play), but something as simple as going to the batting cages or checking out a new art gallery can shake things up without creating too much fanfare. What makes these types of dates so great is that they allow you to concentrate on more than just making yourself sound interesting and create ample ideas that lead to stimulating and insightful conversations about one another.

So we want to know, whether it worked out or not, what's the best first date you've ever been on? Let's share our stories and inspire each other with new ideas to spice up dating. If all goes well, maybe your next first date will be your last.

Tags: dating, First Dates, Adventure, New Ideas
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Post written by RobHeartsDH (View Author Profile)
About this author: Rob lives in Manhattan with his black pug Riley. When he’s not thinking about daddies, he enjoys writing, eating burritos, watching copious amounts of television, and thinking about his next meal.
View all posts by RobHeartsDH


Love this post. My current BF... Our first date was going to Central Park and swinging on the swings on the west side. We literally, walked, chatted and as things came across our encounter, e.g. A bum asking for money, or an illegal sale offer of Corona.. We gave our impressions and got to know each other as things happened... And at the swings, it was fun...and very different than the stale many first dates i have been on where i know what the next question will be already...

While at the swings, we managed to subliminly learn how adventerous we were as in like, he was swinging so damn high i had managed to warn him of the danger of falling haha immediately establishing my role. We got off the swings and walked around more and ate, then went back to the swings only to find them full of children.. He got pist.

Now, since we both love to travel, every place we go, whether Toronto on Degrassi Street, or Oman, we manage to find a park with swings and ride them as our little tradition now. :)

That is so sweet. :)

Thanks, doll!! Xoxo

Having met Rob in Provincetown...I would say any first date with him would be magical.

I believe WE ALL feel the same way about Rob! But it's great that someone actually expressed it.

The best first date i had was taking a guy i met online to a cooking class. It was fun and since he said he liked to eat, I got to show off some of my less obvous tallents... it went well for the most part and the group we were in class with was fun and intersting...I would do it again..
one hitch guys..make sure he is gay and not bi ..cause he ran off with the female instrutor ...and not me...
but I did meet someone else at the class and now we are best buds... so i guess it worked out in the end

Aw i have always wanted to do that with a guy on a frst date. But omg bi!? Ugh! Bi guys, in my opinion, or only allowed within certain parameters of my world in that they are only there for my sexual enjoyment, nothing further! ;))

I've yet to have a true "first date" and I am looking forward to it. What I've read on this thread so far has given me some ideas. There is one fellow I'm getting to know online and he is into art museums and collecting antiques. So I've decided that our first date will be a visit to the local art museum which, to my surprise, he rated as one of the finest in the entire country. I know I'll be learning a lot and also getting to know him first before I know his penis. I will like that.

As much as I like dining out, I think that in future I will choose an activity that involves some other mutual interest my date and I share. In that way our passions can have another outlet which will enable us to get to know each other as complete people and not simply sex partners. Since I want to have a long term relationship eventually, I think this approach only makes sense for me. Hopefully, the man I'll be seeing will have this same point of view. Indeed, that could be a very good litmus test as to whether we should be seeing each other at all.

Hey Geo -
Amazing idea!! I like it. Esp that you know that he has rated the museum the best. Just wondering. Too obvious? Unless u "suprise" him with another set of activity thats near the museum. Thoughts? Just thinking outloud..

Anyway, yeah i think; do a drink and then be like "oh, got us the special curator tour tickets to the latest exhibition". And have thw exhibition be your interest. So that you show him what you r interested in...

Good luck xxox

The best first date I ever had with a guy, was going to an art museum together. We learned more about one another as we interpreted abstract works of art differently.

Some good first date ideas I have in mind: light/easy rock climbing, hiking, museum, bowling, amusement park, watching a play, or an outdoor/art festival.

Good post, however it seems to me that no one really dates anymore. Or at least like to use the word "date."

Date? What's that? Oh yeah, it's a relic from my generation and before then. When someone took the time and energy to make a plan and follow through with it, and make it something a little special. Better stop here, as I don't want to sound like a BOQ (bitter old queen), but I do sincerely hope that you younger guys are having fun with dating and not just plowing through the myriad of faces on the internet and casting them aside without so much as an attempt at a real time meet, let alone a, think of it.

Had sex with a man for the first time three years ago this month. Was married to a woman, came out, divorced. Past three years besides being in my adolescence, had a few coffee dates which sometimes go to my mattress. Thought it would be easy to get a bf and a relationship. Went to my first social mixer three days ago. Met a guy, he kissed me. Usually I am the aggressor. We chatted, he gave me his number. I called him the next night, we spoke for an hour. He suggested lunch this Saturday. He is out of a relationship for seven months, he said he doesnt speak to his X. I had one six week relationship. It was only sexual. I thought I can get more passion, but realize that it is innate. I was a hole to him three times a the math. I stayed because I was burned out from the sex sites. Silly argument, left, best thing. I hope that if we click tomorrow, will NOT take it to my mattress, but meet again for mundane activities and get to know about each other.

I hope your first date was what you wanted - a great time without going to your mattress. There is plenty of time to have sex after you know someone better. And if they don't want to get to know you better, you don't need to have sex with them unless you just need to cum and your hand is exhausted!

If you don't want to go to the mattress, then don't. Some things in life are simple.

One first date that I will always remember was with a guy whom I met via Grindr. After chatting for quite some time, months was more like it, our schedules finally matched for a meeting. Lee was his name and he insisted everything be a surprise. I do not know about you but as a first date goes, being surprised is not what I like to be, but I went along with everything. Lee picked me up at my place and took me to a local park. We began walking the trails which seemed like forever. I started to think I was about to be brutally murdered, hehe. After about a 30 minute walk and almost falling down a steep hill, there was a clearing that opened up to a beach that I never would have guessed was there. Without it being low tide, the beach actually wouldn't have existed, that is how small it was. I was amazed, for about 2 hours we both looked for sharks teeth, horse played, and sat around watching the water come in to high tide. That was one of the best first dates I have ever been on. Unfortunately things didn't progress much further between Lee and I. Apparently he was still in love with his ex, his loss I guess.

First dates and dating in general is a lot of fun. I shouldn't be admitting this but I, myself am a serial dater. I enjoy first dates a lot. There is something about meeting a guy for the first time. Whether it be for drinks, dinner, movie, etc. Seeing the guy face to face, observing his body language, trying to figure out if we are hitting it off or moving more toward the friend zone. Dating is a lot of fun to me. I have yet to find that permanent guy but I keep hope alive.

Scarey as it sounds; my best first date was spent dealing with my date's seizure disorder. (actually the first two dates... but I can explain.) I met Mike in's chat room. He was a fresh faced twink kid of 20; that was living with a man 20 years old than him. His roommate had to travel all over the country with his work; so seldom ever bothered to buy groceries. Mike was working part time in a grocery store (less than 20 hours a week) and trying to pay for food, his medicines and a little entertainment once in a while. The first time I spoke to him; he was online and made a comment about being hungry. Of course all the trolls and users jumped on it and were making offers of getting him something to eat in exchange for a little sex. Mike turned everyone down and logged off. An hour or so later he came back into the room and I said "Hi... Welcome back cutie." Probably 20 minutes later he finally answered me with a short "Thanks... but I'm not interested." I assumed he was just a typical twink and didn't want to talk to someone my age, (I was 19 years older than him.) so I didn't pursue it any farther.

Several days later; I went into the chat room in the late morning and saw he was there. I sent him a private message and asked him if he had eaten anything lately. A few minutes later he came back with "No... he was starting to consider some of the offers that had been made." I replied back that I would be more than happy to buy him a few groceries, just let me know what to get and where to take them. He wouldn't tell me his address (Didn't want a stranger knowing where he lived.) so I offered to take him out to eat... just tell me where to meet him. He had to work that afternoon; but would be off at 5; he would meet me at what ever restaurant I wanted at 6. During the conversation; I found out just how cash strapped he was, so I pushed and said I would pick him up. He needed to spend his money on more important things. 15 minutes before 5; I went into the store where he was working, and bought a small bag of Hershey Kisses. (To lighten up the tension he might be feeling and help him to relax.) When he came out and got into my van; I handed him the kisses and told him this was the only kiss he was going to get from me; I'm a good boy and don't sleep with someone on the first date. He grinned and said "Thanks... so where we eating?" I told him his choice and named off several restaurants in town. After several minutes of discussion; he said he really loved Olive Garden's salads and pastas. So that's where we went.

We spent over 4 hours there talking and eating. (we were the last customers to leave.) I assumed the date was coming to an end when we left, but he wanted to drive around for a while and talk some more. After several more hours of driving and talking in my van; he decided it was time for him to go home and go to bed. He gave me very general directions to his house and had me stop at the corner of his block. When he got out of my van; he handed me several of the kisses back and said they were a token of what he really wanted to give me, then closed the door and ran off into the darkness of the street. I went home feeling tired but happy.

When I got home; I went online to chat with a few friends and saw him in the room. He was talking about the great guy he met and spent the evening with. When he saw me in the room; he privated me and said thanks again then asked me if I had a good time. (Of Course I did.) I told him I had and would like to do it again sometime. We ended talking online until close to 6 am. I gave him my number and told him to call me when ever he was ready to met again. His reply was 'How about now for breakfast." So back out I went to meet him. When I pulled into his neighborhood; I saw him coming out of his house and run down the street toward me. We had our breakfast at a little Mom and Pop diner and talked for several more hours then out of the blue he asked if I would take him home and wait so he could get ready for work, then take him to work.

We got to his house and as we walk in... he didn't make it much past the front door before he was on the floor having a seizure. I got him rolled over and let him seize until he came out of it. (Petit Mal) The second he came out; he started crying and became very nervous. I got him onto the sofa and told him he needed to relax and sleep... he wouldn't be working today. I called his job and told them about his seizure; that he wouldn't be in. When I hung up the phone and turned around, he was fast asleep. I was going to just leave, but I had no way of locking the door behind me. Instead; I curled up on the other sofa and watched tv for a couple hours. Around noon he woke up suddenly and sat up; looked around for several seconds confused; then saw me on the sofa and started crying again. When I got up to see if he was okay; he pulled me down onto the sofa with him and curled up in my arms; then went back to sleep. I dozed off shortly afterwards and slept until late that afternoon. I woke around 5 with him sitting next to me staring at me like he was confused. When I asked him what was wrong he just shook his head and said "nothing." then leaned over and kissed me.

We were together for almost 6 years. I proposed to him on our 1 year anniversary at the Olive Garden; at the same table we had on our first date. As strange as it may sound; Mike is still part of my life and always will be. He is my best friend... we still live together 11 years later and he asks for my opinion of and if I approve of any man that he dates. If I say 'no' then he doesn't see them again. Only once have I said 'No'.

amazing .. living proof that we really CAN take care of each other in this world. Not every relationship of merit has to include sex. YOU put the "daddy" in Daddyhunt my friend ... in the best possible meaning of the term.

Technology has completely altered the dynamic of a "first date."

There was a time--some of you will remember-- when a first date was really meeting for the first time. You knew very little of the man you were meeting, and over drinks or dinner so much was revealed. During a memorable first date of that era, the guy I was with ordered a carafe of rose wine. He asked for a car-fay of rose (as in the flower) wine. I knew then it wasn't going to be a match, but the sex was really good.

Now, those "first dates" are often on-line, quick and relatively painless.

When I meet in person now, it's rarely someone I haven't already connected with on some level. I'll meet someone whom i like the way he thinks. Someone who makes me laugh. Someone who is already interesting or troublesome or difficult. And if his photos don't quite match with his real self, well, that's creative license and I'm all for it.

And because I tend to know these guys on some level, the activity of the first (real) date doesn't much matter. Lunch is best, i think: If it doesn't work you can move on. If it does work you can also move on, in another direction.

I met my late partner in 1990 at a bowling tournament. We were introduced by a mutual friend. Given the situation, it was difficult to get to know each other and, although he was a good looking man, I didnt give him much of a second thought. About a month later, he saw me in the mall, I was working in the GTE phone store at the time. He came in to pay his bill, and left. At least once a week, I or a co-worker would notice him walking the mall outside the store cruising me. I ran into him one night, in of all places, the bath house. We chatted and, of course, wound up enjoying each other. Not much of a first date but we exchanged numbers, met at the beach, spent the day getting to know each other and it took off from there. We were together 12 years, some of it rocky, most of it great. I was devistated when he passed away from a year long battle with lymphoma. Now I'm involved with someone I met online. Our first date was hot sex at my place. We have been seeing each regularly for almost a year and our relationship is growing slowly and in a positive direction. Meeting someone online is not so bad. If it works.....great. If not, then you go back on line and search again. Certainly cheaper and safer than hanging in the bars.

I dated another married man for over 2 years. We talked on the phone a couple of times most days and saw each other once a week for along time, coversation was great, physcial contact was limited,but not bad when it was possible. We both wanted the same thing - a nice guy,with benifits. After awhile my job changed and we we'rent able to meet as often and talking on the phone was alittle awarked, but we stayed friends and had occasional hook ups for another year. Then we had less contact and I found other guys to play with, but looking back it was nice to have the buddy with the benifits arrangment - now that's not possible in my life,and the bathouse is the only time I get to be myself and enjoy other gay men-did meet a guy with whom I clicked and we had a great time, but couldn't swing it with our sechudles and my limitations. So,all you out and proud guys enjoy the prospect of dating and having fun and enjoying another man and his interests.:}

In my almost 57 years of being actively gay, I don't think I've ever been on a "date" per se. Of course, you could stretch the meaning of "date" and, if the sex was good we'd meet again for another date.

Meanwhile, back at the oasis, the Arabs were eating their dates.

I've come to discover recently though spent 20 yrs of my life in 2 LTR's I really have no idea as a gay man how to date and think there many like myself out there .
We first of all tend to first and foremost relate on a primal sexual level .
Men want to test drive a pretty shiny car before we even know if it's really what we are looking for .
IMO sex on a first date if really good can cloud your judgment .
Come on guys how many of you started to date a guy because he was incredible in the sack only to figure out down the road he was total nut or basket case .
We also tend to live in a world of instant gratification which means we want a new bf now without going through the courtship (Guilty as chg) Though we desire someone special in our lives we don't want to put the time and effort into what it takes to make it happen .

Dating is not getting on Ebay and hitting the Buy It Now button and it's shipped to your door in 24 hrs instant boyfriend . It takes time and work and even after months of dating someone it still may not work out. How many reading my comment have been looking for something more out there from a man then just sex for a long time and still single . It time to examine what your doing wrong. Unless someone comes up with a App for dating when you meet someone new ,it's going to take some good old fashion effort and work on both behalves to make it happen . My last BF I met in a hot tub at a vacation resort ,we slept together kissed and cuddled that wkend but no sex . We didn't get to see each other for a month or so after that wkend we live 6 hours apart . Long story short we ended up together 8 yrs . I totally forgot how much work the first 2 yrs of long distant communting was but it was worth every minute.

hmmm well first I'd want to know what is considered a "date". Since many guys meet from on line, in my mind, that has always been a first meeting rather than a date but most guys think otherwise in my experience. I like to keep that first meeting with just coffee and a walk or something. That way we know if we really have some attraction to one another because photos and even the phone just can't account for mannerisms and chemistry that you get in person. After that, the next time would be an actual date and then all the creative ways one can do that should flow. Yes - make it fun!

Why must everything be patterned after heterosexual rituals? Weddings, what point did we stop dancing to a different drummer and hire the straight house band? We can romanticize the word "date"all we want, but it's still two dogs sniffin each others butts. In the seventies and early eighties I saw LTR after LTR that started with a "shallow" bar or sex hook-up. So delaying sex is supposed to somehow show depth or that you want to get to know the person first? Admittedly, I would not wish for a "date" who enters the door appearing so sexually rabid he is like a starved tomcat, but I have also had dates with floridly verbose men who take me through an exhausting travelogue of their lives, or who seem to have a litany of pre-planned questions the length of Gone With the Wind, only to find the sexual "chemistry" a mismatch. Yes, I's "work"...and that is just the problem; how to make it less so is the challenge. I am no fan of the Pussycat Dolls, but "loosen up your buttons." This may seem ironic advice coming from someone whose been poz for 24 years, but I can tell more about someone from the way he touches than a verbal libretto of his life.

that sound so sweet my frist date was with my exbf was in a sexual place where guys look for sex lol

Sometimes, when the event seems to follow a scripted path, it is possible to become bored with the event/process when you're not really bored with the other person. You have to learn how to recognize when this happens so you can change the plans at a moment's notice and turn a stale event into an exciting adventure. That doesn't necessary require extreme sports, but just something unexpected. Like getting out of the restaurant to wander the neighborhood, look at the store windows or the architecture, find an art gallery or a bookstore, and take off in a new direction. I have taken first dates to the zoo, to a museum exhibit, to an art opening and a book reading, in addition to places like my favorite restaurant or cafe. At the very least, doing something spontaneous is more likely to show you the real person behind that perfect "first date facade."

My best first date was from a great boyfriend. We met online through a gay men into outdoor sports website. After chatting and talking on the phone for a few months I flew out to visit him in the spring. He picked me up at the airport, and we stopped by the grocery store for supplies for the next day, the real date. We got back to his house for a quiet evening drinking wine on his porch and enjoying delivery pizza. It was the nervous awkward wondering what to do next.

The next morning he drove us up into the Colorado Rockies with all of our gear and supplies. We snow-shoed up to a little wooden park service cabin at 11,000 feet. It was my first time up in that elevation. Just as we arrived it began snowing. We lit a fire in the woodstove. He melted some snow, got out a wash cloth and proceeded to wash the sweat and exhaustion from my body. We had a romantic dinner by candlelight all alone on a mountain. The next day we skied and continued the amazingly long first date. By the end of the weekend I was smitten for the man. We dated for a year and are still good friends.

I hope all of you have amazingly great first dates like this one.

You Guys are lucky and I am so much happy for you guys....... I am looking for my dream man!!

I think a great idea for a first date is to go to a thrift shop, or a couple of them. You can learn a lot about someone that way, and you're looking at interesting things, not just staring at each other. Plus you can sort of get fresh but in a safe way, and there's opportunity to laugh.

I think the most important aspect of a first date is to find something TO DO other than watch the bubbles rise in an open bottle of beer. Something you can do together, obviously, and not on opposite sides of a net. I personally like short hikes, tours of local points of interest, flea markets and things like that. Winery tours, county fairs, special events all provide opportunities to do something a little out of the ordinary in a venue where you can talk and get to know each other without struggling to find some topic of conversation.

As the day progresses, you can *always* follow with drinks, dinner, movie, and a display of your porn collection.... or NOT.... without any awkwardness.

Being a "beach bum", I like bringing home the "maybe's" for a swim in the pool. That has lots of advantages....

What I refuse to do is meet someone for a drink to see if we "click". I think I'm worth more time a light switch.

I have read all these postings with much interest. And it has occurred to me, that in the age of the internet that perhaps we forgo the word "date", and think of the first time that we spend with someone together. I see nothing wrong with chatting with someone online, using a webcam to make sure the the guy you are chatting with actually looks like his photos. I think in these still perilous times that it is a good thing to know something detailed about the person who initially interests you. It saves being "surprised" and disappointed.

On further reflection, perhaps first "date" is first contact online. Nothing I have written is a criticism of what anyone else stated. At my age, 78, I have learned not to let others ways of doing things prejudice me against them. Since presumably we are all grown up, we can decide what's best for us, on our own, but comments from others can be helpful. It it works, then fine, if not also fine. Every experience can be a learning one as long as we pay attention.

OK.. This is not a 'last date' (which honestly was rather predictable/drab - NOT someone from here, mind you) - but more of a BEST FIRST DATE.

That'd be with my ex - about 16 years ago(?). We met at 3:50am at the Boiler Room in the E. Village - exchanged numbers, and two weeks later finally had a date. We were supposed to meet AFTER the Matthew Shepherd March/Rally in NYC.

I met up with friends for the rally and joined the throngs of random people on the street. Nearly an hour in someone started calling at me - a funny guy named Wylie whom I'd met a few weeks earlier at a party. As we went to meet, I realize he was with some friends… One of whom was my date! The rest of the rally was filled with us talking, meeting each other's friends, holding hands and making eyes at each other - in betwixt shouting at police, listening to bull-horns and being New Yorkers (he is an Manhattan native as well - a rarity).

After the rally we grabbed some food and went back to his place for a VERY nice long make-out session. We were together for nearly 12 (mostly very good) monogamous years. As a bonus, I came across (and recorded!) footage of us marching together in the crowd from a gay Public Access cable news show! Transferred it to my computer - and printed a screen grab of the two of us together on that day. My relationship with him still holds a very special place in my life and heart.

The last first date I had was set up by friends. They kept telling me about this nice guy they wanted me to meet and how they thought we were a good match. We talked and set up our "date" to have a nice long walk along the beach to get to know each other. During out walk he only got 5 phone calls and used the bathroom twice. The walk was good but thee was no magic not chemistry and we did not click at all. I was not a happy camper and my friends got told off by one very unhappy bear. I did get one follow up phone call from him letting me know that he was busy working and would call me for a second date. That was 7 months ago I was not holding my breath to get that phone call. I am still looking for the man who can take my hand look me in the eyes and tell me there is nothing you can ever do to lose my love.

My last first date....

Was magical. I was one super lucky guy. It was summer, and he took me on about a 4 hour drive (I was unaware of where we were going which made it all the more.... special?) Anyway, we arrived at this huge open field, about an hour before sunset and I instantly got told we'd have to hurry up if we were to make it to this "place" on time. We began to hike up this mountain for about an hour and when we finally arrived at the destination, we walked behind a rock to see quite possibly the most amazing, breath taking, completely surreal view of the countryside. We sat there holding hands and getting to know each other for about 3 hours. We had food too (It was only crisps and chocolate) but I wouldn't change it for the world.

Thats the only date I've ever been on, so I doubt many guys will come close to topping that, but It'd be a day to remember if anyone did. Its a shame the guy that took me on that date didn't value me as much as he should have..