Easy answer: I don’t. My last relationship ended about 5 years ago with me getting cheated on, and since then I haven’t really bothered. I’m just trying to focus on myself.

I didn’t read the body of the message so this is a joke responding to only the title:

With a calendar!

(Seriously though I’m polyamorous and a calendar is basically a necessity)

Since the days of IRC a lot of my dates and relationships either started on or crossed the digital realm. As young men, it was difficult to distinguish between sexual attraction and emotional connection. I ended up in a lot of weird relationships because of sex. I never counted the number of dates I had with someone before progressing things, I don’t do that kind of thing The women I was with didn’t count either. I guess we just go by what feels right. Maybe it takes a single day, maybe it takes a month. Whatever works.

How long does it take for you to know if you’re attracted to someone (sexually, romantically, emotionally, shared interests, etc)?

Sexually attractive? Less than 5 seconds. Emotionally invested? Impossible to know, it varies tremendously.

What do you like to do when you date and does it change depending on how many dates you’ve been on or how well you know the person?

The first thing to do would be having sex plenty of times. And that’s not just me pushing or anything, women love sex too (of course). A lot of times I would like to take things slow in that area, but it is difficult to resist. Other than that, I love cooking for them and watching TV shows. I guess I’m basic.

Once you start dating someone, how long does it take you to understand whether you want to date the person long-term or whether it’s not going to work out?

I never know if and how things will work out… how can anyone know? Sometimes I have emotional reasons to stick around, I’m charmed, infatuated, or in love… but I don’t have a crystal ball!

Do you only date people you meet in real life or do you use dating apps? How do you approach going from stranger to dating them?

I have dated people I met on IRC, Tinder, and a whole slew of old-school or defunct platforms. Probably more people from the real world overall, but not by a huge margin.

I’m pretty good at approaching women, but I do it very rarely. Usually when I already know something about the person and know that it will probably pay off. So it is incredibly rare, but, because I am careful have ways to check beforehand, my success rate is relatively high.

The way I approach this is through “sensible honesty”, so women always know my intentions but I don’t throw it at them at inappropriate times and circumstances. And I’m not pushy, I’ll back away at any sign of resistance or rejection. And I give them lots of chances to reject me. So I’m super obvious and clear, but never forceful or inconvenient.

What’s most important in deciding whether you want to date someone? Do they need to have an interest in activities you enjoy, shared values, emotional intelligence, a certain kind of humor, or something else?

Physical attributes are where it begins, but I must note that what I consider attractive is not necessarily very mainstream. Starting because, since an early age, I appreciate plus-size women very much. Also, cuteness is way more important to me than conventional “hotness” – because to me being cute is the same as being hot. When we started dating, my partner used to send me a bunch of nude pictures in stereotypical “I’m so hot” poses, a lot of cleavage, etc. That didn’t do it for me. The day she sent a picture in a cute pajama… it drove me insane!

Is there something you don’t understand about dating and want to share your frustration?

Not really. Compared to other human activities, dating is fairly simple. There are clear rules and patterns you follow. It’s kinda like a script with some improvisation in between. Most of my socialization troubles happen in highly informal, spontaneous, “unscripted” situations. Dating is not like that. It’s a narrative – it can get complicated, but it still has a beginning, a middle, and an end.

“Is there something you don’t understand about dating and want to share your frustration?”

Literally all of it. I do not date full stop. I haven’t gone on a date in over a decade, and before that experience it had been another decade. It’s almost certainly never going to happen again. I don’t understand anything at all about dating. How do you meet people? How do you enjoy time with them? What is even going on?

@Gaywallet I only date myself, haha.

I am 28, soon to be 29, and I’ve been single for almost 5 years if I’m not mistaken. I’ve gone to Tinder, Bumble, Alovoa (despite no hot singles in my area there, haha) and I just grew disappointed. Every time something happened with a girl, we would just hang out for a drink, then went home and never spoke ever again. Either she didn’t like me, or (in a couple of cases) I didn’t like her.

And it’s not just the physical aspect that I am interested about somebody (although it does play a significant role). It’s also about how well we click. About the way we think about things, about what our passions are, our interests etc. If those don’t match, then nothing can come out.

I’ve been in a relationship for 3 years before. She looked great, but I saw we saw things quite differently. She was quite pushing for a long term thing, while I just wanted to take things more slowly. Also, she was a bit possessive as well, and didn’t quite like that I was hanging out without her - despite the situation didn’t even allow her to be there.

Then at a previous job that I had, I met someone that fulfilled all the criteria. I didn’t do anything with her outside of work, besides hanging out a few times and talking on WhatsApp, then on FB, but I realized I was spending better times with her than with my ex from then. I tried changing the situation, that didn’t work, so we decided to part ways. I’m still in touch with that former colleague, but I was too stupid to try something out with her in time (there were also various circumstances, but still), so she found someone else, and now they moved together since a few months ago.

Most of my dating experience as of late was after that moment, but I never found such a person again. I just wish I had a time machine, so I could go and tell myself to act at that moment.

My advice (and answers to your questions):

1. You just know. You just feel that the person is the right person. Interact with that person some time and see what you feel about them. It’s okay not to be attracted by someone. I’ve met countless persons that I just had opinions that they just appeared not okay to me at all. I personally still crave a relationship, but at the same time I’m aware that not having similar visions about the world is not going to cut it long term. So I just lose my attraction in them altogether.
2. If she’s a person that I don’t know that well, I generally go to a place where I have the opportunity to meet her better (generally a park or somewhere where we can drink something). If I already know what she likes, I pick a fun activity. But yea, as I am disappointed in dating, I am out of specific ideas.
3. I learnt to figure it out even from the first date. But 2-3 dates would generally be fine as well. Then, again, I am also quite a friendly person, so I might keep in touch even after if the person is okay enough. It’s complicated anyway, it’s not about time, more about how I feel, as I said above.
4. I had the biggest success in real life. I met my first gf at a concert, as she was the friend of the gf of a good friend of mine. The second I met in a pub, brought by a friend of a friend from the group we hung out with. Then, the third (which was the one I spent 3 years with), was talking about some classes on the hallway of my college, and the fact that she needed a course. So I just jumped into the conversation and said I could help. My former colleague that I wrote about earlier just looked great, and I just joined the conversation with her. It was her first day of work (or something like that, I remember it was in the first week of training) and she told me she just broke up with someone the other day. So I thought about being a bit flirty with her. I also found out we were studying similar stuff on college and that she also knew Russian and was into politics and had similar views. And as we were still talking, I ended up actually liking her. On dating apps, I did not have the same success (as said earlier). But I tried them because I had nothing to lose in real life. Nowadays, I’m just no longer really using them that much. I feel they’re a waste of time and that you just can’t have genuine feelings on these. You cannot comfortably attach to someone there and not be dumped, either by ghosting or by being unmatched altogether - albeit this can also happen in real life in a way or another, so they can also be a good lesson.
5. and 6. - I wrote about these earlier.

Sorry for the long post. Hope you’ll be more lucky in finding your half than me 😁

I use a calendar… to check how long has it been since I dated someone 😐

Anywho, once upon a time…

It takes me about 10 seconds to know whether I’m attracted to someone or not. We used to play a game of “what are they thinking” as kids, and it taught me to instinctively look for micro expressions, how someone moves, how they talk, where they look, etc. to figure out a general personality profile, with a range of possibilities of how they will react in several situations.

Generally speaking, I get attracted to people whom I can’t “read” in that way.

Whether I’d want to date someone long-term or not, boils down to how long it takes me to get a “read” on them and be able to predict their behavior. It may take a day or a month, but when I can predict every next disagreement, and there are not enough shared interests, it gets me bored out. Even with friendships, being able to predict every disagreement and every response, becomes tedious after a few years and makes me drift away.

Some other compelling reasons, like a murderous ex, or getting sick and not being able to travel to meet, can also cool things down quite fast.

I’ve mostly dated IRL, with one exception. Sometimes I met them first online, but that usually didn’t do it for me, I had to meet IRL to get interested. The one time 100% online, was not from a dating app, but from a forum… with a somewhat convoluted story I don’t want to talk too much about (it didn’t work out in the end anyway).

Some shared interests are a must, ideally with non-shared interests that complement each other’s. Some shared values too, or at least not radically opposite ones. Some basic emotional intelligence is important, but I can deal with some lack of it… and while I don’t ask anyone for their IQ, over time it’s turned out that only above-average seems to work (I’m guessing that’s why I can’t “read” them in the first place). I’d put sense of humor along interests, with one exception: laughing at people, for something they aren’t responsible for, is a red line. I don’t have a body type, but extremes make me wary. Another red line, is smokers; I can stand some second hand smoke, but I’m not dating an ashtray. Same for alcoholics and other drug addicts. Curiously, I can’t smell marihuana, or truffles for that matter, so that wouldn’t necessarily be a problem… but I’ve noticed marihuana users tend to get on my nerves both when they aren’t high, and when they are (not exactly sure how that works).

And I guess I don’t really understand online dating, or whatever there is any chance for people who are depressed, sick, and kind of broke (as in, I wouldn’t date myself right now, so why would anyone).

I met my wife through friends, not through massive amounts of dating. After first date with the woman that ended up as my wife, I mentally gave it two months. Some where along the way it got out of hand and we have been together for 28 years. Who would have known.

Personally I do not believe immediate attraction is more then lust and lust is not a long term thing. You have to get to know people and that takes time. If you know someone and can accept them for who they are your likely to love them. Then there is the question whether you can stand them, do you trust them, are your lives compatible. If your lucky the lust part comes and goes and comes back again over the years but it is not the basis of our relationship.

It feels a little weird commenting since I’ve been in a committed monogamous relationship for twelve years and am “out of the game” as it were. That said, maybe that’s where some folks hope to be and I can be helpful in some capacity.

How long does it take for you to know if you’re attracted to someone

Physical attraction is fairly instantaneous. Some people are just gorgeous. The rest happen rather asynchronously and asymmetrically if they happen. Shared interests have tended to coincide with emotional attractions, but more often than not have been friendships with common passions. Romantic attraction relies on all the rest, plus intellectual engagement.

What do you like to do when you date and does it change

My own tastes have changed over the years, so the activities I would and do take people on have changed as well. Experiences with occasional pauses are better dates if it’s not just sitting somewhere and enjoying the company, in my opinion. Concerts, plays, walking around an unfamiliar town until you get hungry and backtrack to that cute place fifteen minutes ago, all good options. The first date with my wife was at a bookstore/coffee house (yes I’m old) where we grabbed a book about having successful first dates and answered questions in the book honestly or to crack jokes at our discretion. We still go out to art/dance parties with glow toys even though we’re sometimes among the oldest there. The important thing is to have fun doing something with someone. Redundant emphasis on the “with someone” - fun times are great and all but it’s having that/those particular person(s) there that makes it special.

Once you start dating someone, how long does it take you to understand whether you want to date the person long term or whether it’s not going to work out?

Sometimes it’s not very long. The relationship with the person who sent arrival texts saying “I’m hear” did not last long, at all. Other relationships lasted far longer than they possibly ought have, until it was glaringly obvious that we weren’t helping each other anymore. Personally, I have found a second and potentially third argument to be illuminating when the chemistry and interests are there - with a first argument there are so many built in expectations on either side that have never been paired that it may end the whole thing on its own.

If the attachments are strong enough to have a second argument, has each person adapted to the other(s)? Is it an airing of grievances between equals in the hopes of a resolution, or is it an aggrieved power struggle? Have those involved grown enough as a team to build towards something rather than tearing it down? I’ve said plenty of things I regret later, more than I’d like, and there came a point where I lost interest in the adrenaline of those moments and found myself prioritizing the ability to have productive disagreements instead of fights. It took a while to find someone who was able to have those with me, and it’s been worth it.

Do you only date people you meet in real life or do you use dating apps?

Every relationship with another person is real, whether it’s online or AFK. I prefer the in-person variety. The relationship with my wife started on a dating app, but only after I had had zero successes and said “eff it, this is for me to have fun with”. We spent time only messaging through the app, then to personal emails and in person.

How do you approach going from stranger to dating them

Have a good time with someone -> starship troopers meme. Find out something they like and wish more people liked, then do that with them. Next time, share your something with them. Find things neither of you have done but want to, and do them. If you’re having fun with each other, keep doing that. Have a good time together until you don’t, and discover together whether it’s something that will pass.

What’s most important in deciding whether you want to date someone?

For me it’s been all of these, with the addition of dreams/goals/aspirations - I want to be with someone I believe in, someone I can get behind and encourage to be the best them they can be, and I want to be the sort of person towards whom those intentions are reciprocated. Granted, that bit can take some time to uncover, but it’s an important piece.

Damn good question. No answer for you, but good question.

“Varies” for all bar the penultimate.

There it would be less “deciding whether you want to date…” and more “deciding whether you want to continue to date”. Am a bit hasty when it comes to getting embroiled before scoping stuff out.

Activities are nice, but unimportant.

Values very important - they don’t have to align on details if they’re broadly shared, but I’ll be revulsed if someone pretends to be more aligned (or more freshly & speedily persuaded than they truly are - we all change our minds, but if you volte face too readily I’ll query your sincerity & also the depth of anything you claim to believe, past, present & future).

Emotional intelligence? For the most part, if you’re aware of & working on your insecurities, encouraging me to work on mine (sappy contradictions are a waste of breath & mental energy) we should be ok. Playing games is anathema to me in both directions - I’ll come to you in straightforward terms if I have a problem and expect you to do likewise. Until then, assume I am content with our relationship.

Humour? Overlap is lovely, but you need to have some even if we have no mutual sense of humour. If you only crack insincere smiles & never once laugh, despite a great variety of social circumstances, imma have some misgivings unless there’s reason to suspect anxiety or depression.

N.B.: yes, all of the above are things discovered in my dotage as an experienced lady, on a recent escapade, now mercifully over.

I wasn’t going to comment on this because I’ve been in a monogamous relationship for 15 years at this point, but one thing I noticed in the comments is really interesting to me.

Pretty much everybody is saying they know they’re attracted to someone physically/sexually right away, and that was not my experience when I was dating regularly. Maybe I’m odd, but I always found that most of the time I would get to know a person first and then I would start to notice things about them that I found attractive and kind of mold my way of thinking and looking at them around those things that I was attracted to in them. Sure, there were exceptions, there are people out there where I was just like - damn everything about that person is hot (my wife being one of those) - but I dated women with a wide variety of physical features and really the only commonality was that I liked being around them. The physical stuff was secondary (although still important) for me.

it’s been a minute since i’ve dated around, since i’ve been with my current partner for nearly eight years. but i love dating, even awkward first dates.

• i’d say i tend to know pretty quickly, like a date or two in. sometimes the first date if we really hit it off.
• i like getting a drink or two for the first date. low stakes, and i can make the excuse that i need to let my dogs out if i need to ditch it quickly. later, i like activity dates like swimming in the lake, a bike ride, hike, or rock climbing back when i used to do that. once we’re established as a couple, i love movie dates!
• tends to be a couple of months. once i see how our schedules mesh, if they’re willing to compromise with me on certain things, meet some of their friends, etc.
• i’ve always used dating apps. child of the internet and all.
• shared values for sure. physical and sexual attraction are top tier as well. i used to think money didn’t matter, but after dating somebody with a very different income, it was tough for things not to feel imbalanced.

my partner and i still go on dates once a week. :)

That’s the neat part: I don’t.

Let me see if I can drag this dead horse into the conversation …

I’ve never met with success trying to find a partner. They show up at the oddest of times, pretty much exactly when I’ve given up. And, to that end, I’ve been on one “successful” date, inasmuch as we lived together for a few months. But she turned out to be what I needed to get used to cohabitation again ahead of meeting my first wife.

I’ve been fully and inescapably in love twice. Once in 1998, and the other in 2009. In both cases, not only was hooking up not the goal; it was actively against either the situation or what had been agreed to. This oddly provides something of a comfortable situation to be oneself without artifice.

The 1998 story is a whole bunch of random shit had to happen just so for me to end up meeting her (she was nominally my boss for nine days while I designed my first newspaper pages). She did not want to hire me and was forced to take me on by the ed-chief, who rightly pointed out she needed staff, and that as a school paper, that meant bringing on people with zero experience.

She continued to be my boss, but that was really sort of a moot point by the time we put the paper to bed, had a 2 a.m. dinner with the rest of the production team and went home together. Nine days. She had her place, I had mine, and it was immediately clear we were overpaying for housing as a result.

Now, if 1998 required all of these specific things to come together, that was amateur hour. That was just upbringing and specific timing on being edited for a news story by the EIC because the news ed was at lunch. It was the end of a call he took as I left, where I heard only one side (this was a landline call) that included “yes, we are looking for designers.” I turned around from the door after hearing that and mentioned I might be interested.

I have no doubt that without the social aspects I found myself thrust into, I would not have ended up in journalism. In under two weeks, I had a circle of friends, a girlfriend and a calling.

Now, as I said, amateur hour.

The second wife, that’s where everything really comes to bear. It requires everything from the first chick I fucked to I-5 freezing from Ashland to Tacoma. Oh, and about five years, as I initially reached out to her before getting serious with my first wife. She wanted nothing to do with me and sort of told me to go find my own kink adventure. “I really have no interest in teaching anyone.”

So there I was, crashing on a friend’s sofa ahead of the holidays, trying to find work and maybe a little fun on the side. I started talking with this ex without knowing I’d already contacted her (different OKCupid account on her end) and been shot down. I’d worn out my two-week estimate for saying with him several exits back, and our conflicting definitions of “out this weekend” led to a chain of events.

I had one night of the unexpected two covered with a former coworker, but there was one glaring hole ahead of getting up to Tacoma so my lesbian ex could fuck me and then abruptly leave to admit all that had happened to her wife. She’d already played this game once before, driving down to Medford, getting a hotel room and then … crying and driving back. But her sister worked for Marriott, so I had the room with neither of us paying … I just needed to cover Saturday night.

And so, as one does, I reached out to the chick who was engaging me because I mentioned on my profile that I still slept with a stuffed animal. “Fancy a visitor?”

She can likely better explain what compelled her to say yes, but she did. She lived on the coast and was thus a logical stop for the night while I enjoyed the unfrozen 101 on my way up. She did want to know one thing: Did I contact her specifically to fuck her? Because that wasn’t going to fly. And no, at that time, I did not.

The problem was readily apparent upon walking into her kitchen. Oh, she didn’t realize it yet, but I looked at the magnets on her fridge, just a glance, and what was immediately core-of-my-being was “this is not the last time I’m going to be in this room.”

And this was absurd, because I was introduced to her kids as “an old friend.” But as one does, we watched both Labyrinth and The Neverending Story, part of the way through which she, having made sure I was not there for sex, said, “You know you can touch me, right?” Which isn’t as dirty as it sounds and also totally out of character for her.

So I timidly grabbed her hand, and at this point, all was lost. It was like touching a part of me and thus quite weird. She had the same reaction, which would in a week be somewhat of a bad time for her then-boyfirend who’d come down for the holidays.

But it wasn’t settled yet. That would take getting up to Tacoma and having a six-hour call in which it became clear I was going back to Oregon.

So, dating? Yeah, that can be rough, but I prefer skipping that whole bit and just waking up next to someone who was apparently just waiting for me to show up.