So how does this dating thing go?

June 24, 2010 9:25 PM

I'm pretty new to dating, and I don't really understand the progression from first date to second date and onward. Can you help me cure some of my ignorance with your anecdotes, personal experience, and wisdom?

Obligatory background: I'm a guy in my 20s who's been in a few relationships in the past (that grew organically out of friendships), but who has never really "dated." I live in a city in the midwest USA.

I just started to use OkCupid a couple of months ago. I tend to go for girls who seem similar to me (a little introverted, intelligent, a little religious), and I've been on ~10 first (coffee) dates with different ones. I've been on one second (dinner) date so far, which I feel I might have treated too much like a first date, and tomorrow I will be calling another girl to ask her out on a second date. I have a much better feeling about this girl than any of the others I've seen, and I think there's a good chance she'll want to see me again.

I know first dates are supposed to be about getting to know someone on a somewhat superficial level and to see how you get along in person, and I've had enough practice to work out the mechanics of doing this in a coffee shop. I have a lot of questions about what happens next:

1. What makes a second date different from the first date or a third date different from the second? How do things "escalate" from date to date?
2. From the first date, I know where she works, what she does for fun, what kind of food she likes, the basics about her family, etc. I feel that (n≠1)-date conversation should progressively go a little deeper, to a point. Is this correct? What are some things I could talk about to go a little deeper? I know I can mirror her if she goes a little deeper, but that strategy would result in a stalemate if she's mirroring me.
3. If we have chemistry, during which date should I start looking for first-kiss opportunities? Should the first kiss be a peck on the lips or more? What locations are appropriate (i.e. what if we met each other at a restaurant)? In earlier dates, should there be any buildup to this (i.e. hugs, etc)? Basically, I don't want to push things too quickly nor put them off for too long.
4. After the first kiss, what's the time-frame I should be thinking about making out? Sex? Again, I don't want to be too aggressive, and I know everyone is different, but I want to have some vague idea of when these milestones typically occur.
5. What other etiquette things should I do? If we meet should I walk her to her car? When is it appropriate to pick her up at her place?
6. How should I work in fun stuff? My activity progression right now is coffee -> dinner -> ???.
7. How much time should pass between dates? How frequent should they be?
8. Between dates, should I email or call her, just to chat? So far, I've been stopping online communication once we've made in-person plans.

I understand that this stuff works differently for everyone, and it's a fools errand to try to "script" things, but right now my mind is a big ball of blankness, and I'd like to get something in there to avoid some bothersome trial and error.

posted by dogcat to Human Relations (16 answers total)

Best answer: 1 - generally, there will be more physical interaction; hand-holding, that sort of thing, that tends to presage more emotional involvement
2 - I find it's a bad idea to walk into a date with a list of things you will talk about. But a really good question is after she says something, or after you say something, "What do you think about that?"
3 - I think any date, if there has been contact leading up to it (see point 1), is a good time for a first kiss. A private location is best, to allow for either a lovely and uninterrupted moment or to avoid embarrassment if you read the signals wrong.
4 - this is different for different people. In my dating experience, there tends to be a give-and-take back-and-forth about when is good for what. Bear in mind I'm gay, and the physical aspect of our dating rituals tends to be slightly more... compressed.
5 - treat her like a decent human being.
6 - "Hey, would you like to do a Fun Thing?"
7 - as often as your schedules and desires mesh, frankly. For some people that's once a week, or once every two--or every other day.
8 - I certainly don't see why not.

As for avoiding trial-and -error... that's what dating is. You're both trying each other on for size. Be who you are; it's going to come out if you keep seeing each other anyway, so don't try and script things or be something you're not. Personally, I find awkward nervousness incredibly adorable, so maybe I'm in the minority here.
posted by dirtynumbangelboy at 9:33 PM on June 24, 2010 [3 favorites]

Best answer: Like you said, this is totally dependent on the two of you. All of these things could completely go out of the window, but I think they're fair estimates from my experience (woman in my 20s, dated mostly in the Midwest).

1. Early dates are for getting to know each other and figuring out if you like each other. Your sense of each other should thus progress from date to date.

2. Yes, they should go deeper. See answer to question 1. Things that are critical for her to know should come up before she'd need to know them but not too early. If you have oral herpes, this should come up before you kiss her with a cold sore. If your mom is schizophrenic, you should tell her before she meets her. However, you shouldn't tell her intimate details until there's trust built- that may freak her out. I'd temper this with your comfort level with her. So you should be telling her things based on a sense of appropriateness and your comfort level with her, not necessarily directly based on how much or little she's disclosing. One thing that is helpful is to really focus on listening to her and asking a lot of questions.

3. I think second date is completely safe for a kiss. If you meet her at a restaurant, walk her to her car, give her a hug, and then gauge her reaction. You could go in for a kiss if you feel like it would be mutual. It's OK if she's not going for it- this can be awkward and people tend to back off rather than pushing themselves to go for it. Watching a movie together/having a post-dinner drink at one of your houses is code for "I'd like to kiss you, possibly more." If you watch a movie, you can do the progressing levels of touch thing.

4. I get the sense from my friends that 3rd date is pretty average for fooling around, 4th date is average for sex.

5.It will really depend on her and whether she feels respected or patronized by chivalry. Walking her to her car is generally fine, I think, while insisting you walk on the street side of the sidewalk is not. Don't pick her up at her house until at least the third date, and then ask if she'd be comfortable with it.

6. At this dinner, you can pay attention to what she says her interests are. If she says she's been meaning to/wanting to do some fun activity, suggest that you do it together sometime. Ideas are hikes, sports, museums, going to see a band, checking out a local bar, etc.

7. Probably not two nights in a row. Once every 5 or 6 days would be fine.

8. Yes, you should, but not every day. Let her contact you first some of the time, then the ball's in your court again.
posted by emilyd22222 at 9:50 PM on June 24, 2010

I found that when I had to think about these sort of lists, it meant that I was trying too hard with a person who was not a good match. When I didn't feel the need to script it or have some big plan, I was comfortable with the girl and just tried to have shared good time experiences types of dates. At dinner we would be laughing and talking about our favorite ice cream shop and I would say, "Lets get a check and go to said ice cream shop for dessert." It sort of flowed naturally.
posted by JohnnyGunn at 9:50 PM on June 24, 2010 [10 favorites]

I would suggest not worrying about the answers to any of these questions, because there aren't any concrete answers to be had. Women are not robots and relationships are not reproducible science experiments. There is no secret formula.

If you are on a date, and want to hold hands - hold hands. The same goes for your other dating questions. Your date will let you know if you are making missteps, or are moving too quickly. React accordingly.

Relationships should be organic. Relax.
posted by axismundi at 10:11 PM on June 24, 2010 [2 favorites]

ha ha, i had a big old list typed out then read johnnygunn's and that was perfect. you're thinking about it too much, and maybe forcing it a bit.

online dating is a numbers game. go out with three different women over the next week without any physical motives or anything, nothing manipulative. message some women who are a bit more outgoing than you, more/less religious or whatever. mix it up a bit. don't think about it. message someone you think is out of your league.
posted by rhizome at 10:19 PM on June 24, 2010

Guh, OKCupid....


Uh... what do you want out of this? You wanna bone a chick or do you want grandchildren, eventually?

I think your questions need only be answered by, "Be coooooool". There's some cheesy 80's movies about that, but I think you got to leave the neurosis at the door and just enjoy yourself. Be real, honest, truthful and yourself. Anything else and you're playin' a game. And there's a movie about that, too.
posted by alex_skazat at 10:30 PM on June 24, 2010

yeah, johnnygunn said it better. the best dates/dating is/are organic. I went on a date last week which was awesome; we (I) planned it, but we ended up hanging out for something like eight hours or something.

Let it flow, man. If you have to force it, in my experience, it's not really going to work--because you will alwayshave to force it.
posted by dirtynumbangelboy at 10:30 PM on June 24, 2010 [1 favorite]

Oh. I'll also say that the whole "progression" thing is bullshit. Just go for it, if you're feelin' it and if you ain't, don't go for it. Rules are for tools. I'm not a big fan of "dating", it's rules set forth by people who have nothing to do with me, in a culture I really don't 100% agree with. It's just another thing in life that needs serious questioning and the answer is going to be as unique as you, and me.
posted by alex_skazat at 10:32 PM on June 24, 2010

Like JohnnyGunn said, I think that when you click with someone you don't really need to bother thinking about lists & rules much because things will just flow of their own accord. Bear in mind as well that you will probably not be flying solo, either - she would be maneouvring the situation as much as you, if you're both on the same page (um, of a picture book that's about flying).

Just as long as you don't do anything egregiously weird (like contacting her incessantly or inviting her to naked mini-golf with your parents) you should be fine.
posted by UbuRoivas at 10:32 PM on June 24, 2010

I found that when I had to think about these sort of lists, it meant that I was trying too hard... It sort of flowed naturally.

For some of us it will almost never flow naturally without lots of work, I think. Whatever "politeness" is in my head, probably a mix of social anxiety coping mechanisms and coping mechanisms for other insecurities, it clamps down and forces me into a pattern of interaction with someone I have never met before that I think must effectively hold them at an arm's length emotionally, a distance which in practice never recedes in most cases. My brother is much more attractive than me in a number of ways and has much more short-term luck with women but still speaks of something similar in an inability to flirt. (Though he occasionally acts playfully and teasingly with other members of our immediate family, unlike me in his late twenties he has only one long-term friend to be that way with.)

Although I'm capable of quite intimate friendships and other intimate relationships they seem to happen very rarely and only after I've gotten to know someone through casual contact over many years. So I think that extensive planning and mental rehearsal with modeling information like this question asks for is probably necessary to overcome my habits, mental attitudes, and reflexes that would prevent intimacy from developing quickly enough on the time scales you have when you meet new people.

So thanks to dogcat for asking the question and to everyone else for taking the time to answer, it's very helpful. Wish I'd been able to coalesce my own thoughts well enough to ask this sort of question myself. Perhaps at this point, as dnab says it will never work because I always have to force it, I at least feel like I'm always making incremental improvements thanks mostly to insightful answers people give to AskMes.

(One last anecdote - I have encountered people whose behavior seems to be the inverse of mine: they seem to be immediately intimate in the way they interact with other people and even appear to be unable to back off and be less informal. On these occasions we're just completely baffled by each other's behavior and stare at each other like the other is a Martian.)
posted by XMLicious at 10:53 PM on June 24, 2010 [4 favorites]

Response by poster: I get that it should be organic, unforced, etc, and I plan to be like that. What I'm trying to avoid is figuring everything out from scratch on my own. I want a better idea of the possibilities for action, social mores, what I could do, etc, so I don't have to spend as many brain cycles figuring them out. To give an example, if I want to kiss a girl for the first time, I want to have at least a few pre-formed ideas about how I could do that, so when the time is right I have more of a choice between options than a problem to solve.

Basically, I want a vague idea of what I could do next in my head, instead of a big blank unknown. I will be doing a lot of learning by trial and error, that's unavoidable, but I think it would be great if I could pre-fill some of that void with a rough sketch, so I can start working on the details now, instead of the outline.
posted by dogcat at 10:58 PM on June 24, 2010 [1 favorite]

Response by poster: The lists are great, like emilyd22222's, because they give me ideas (especially ideas like, "whew, it wouldn't be odd if I did that"). Ideas and distilled experience are what I'm looking for here, because those can serve as a starting point for my own experience.

While I appreciate the intent, admonitions to "be yourself" or "it should be natural" don't really meet that need.

And I am definitely not looking for a script that I can follow like a robot, and I'm not asking with any particular girl in mind, it's just that I'm just now getting some new situations.
posted by dogcat at 11:19 PM on June 24, 2010

While I appreciate the intent, admonitions to "be yourself" or "it should be natural" don't really meet that need.


Well.. the problem is that is the distilled experience, in my case anyway. It's going to be different every time. Sometimes you want to kiss someone the very first moment you see them on your first date--and sometimes they're receptive. Sometimes they want a very specific and formalised courtship ritual. Sometimes they don't.

In general, sure, many people don't fuck on the first date. And generally speaking one progresses through layers of physical and emotional intimacy. Usually it's a bad idea to overshare before trust has been established.

But it really does change every time. I've been on very formal dates--dinner, a movie or a concert, a kiss goodnight at his door or mine, followed by gradually less-formal occasions. I've also been on totally impromptu random dates that involved making out in a movie theatre, with the second date being a more sedate and well-behaved night at a concert.

The thing about 'it should be natural' is that it is so often true. I know you think this isn't helpful, but it is. Perhaps the best way to look at it is that you're developing a friendship--which in a very real sense is exactly what you're doing. With any kind of relationship there is deepening emotional and physical intimacy, whether the latter is sexual or not. So think about your friendships, think about the good ones--how have they developed? Was there planning and forethought and 'I must do the right thing', or did they evolve organically? With the caveat that friendships aren't as socially regulated/ritualized as dating is, you're looking at a good model there.

The problem is, you're asking about expectations--date frequency, should I call--that will be different for every girl you date. Some of them will be very The Rules types--kiss on the first date, three dates before making out, call 48 hours after the first unless it's a full moon in which case check your local tide tables. I personally find that ridiculous. Some girls love it when a guy calls the next day. Some don't. Some love emails and random calls. Some don't. The thing you have to do is ask them. There really is no rulebook except the one called Your Expectations and Her Expectations: Where They Meet, authors You and Her, multiple editions available. "Mind if I give you a call tomorrow?" is often a good question.

In general, the Official DNAB Dating Manual runs thus:

1 - Be yourself
2 - Let her be herself
3 - Follow your instincts, but
4 - Pay attention to how she reacts, and
5 - Adjust accordingly while remaining mindful of Rule 1.

I know, I know, you're going to say you don't have instincts. But you do. The vast majority of people can at the very least pick up--if they're paying attention--whether someone likes their company or not.
posted by dirtynumbangelboy at 12:24 AM on June 25, 2010 [5 favorites]

Best answer: One thing: If you're thinking "is this a moment I should kiss her?" the answer is "YES!"

I have to many times that I was out, did not go for the kiss, and looking back it was clearly the exact right time.
posted by jander03 at 6:40 AM on June 25, 2010 [3 favorites]

Best answer: Practice makes perfect. I've been on over 40+ internet dates (less than 10 progressed to a second date for various reasons, my choice, their choice, whatever) and you just kind of learn what to do and what not to do. I am very literal and very bookish/manual-ish and I wish I could have read a "how to" beforehand, but it wouldn't have worked. Just don't sell yourself short, be safe and roll with the punches. And be kind. If you don't like someone, tell them early on and be as kind as you can even if they wig out. It can be super frustrating but I bet you will have some great stories.

IRL examples of what NOT to do!

Guy: I'm Jewish and that's super important to me... #cultural thing, #religious thing, #more stuff.

Me: Can we sleep together just to piss off my Irish Catholic grandma?

****

Me: Thanks for the coffee. Nice to meet you.
Guy: I'd f*ck you, just you you know.

****

Me: I'm a Spanish Major.
Guy: I hate Mexicans. Damn wetbacks.
Me: Uh, I have to leave to go to a party that starts soon.
Guy: Can I go too?
posted by ShadePlant at 8:04 AM on June 25, 2010 [1 favorite]

Best answer: 1 - I would say that the second or third date should definitely be some kind of activity, rather than just dinner. Dinner dates can become very awkward very fast. Once you have an idea of something the gal might be interested in, suggest that as an activity. Ideas include art galleries/museums, music shows, putt putt, bowling, movies etc - you get the picture. Movies are fun, but they don't really allow you the opportunity for conversation or fun interaction. Some kind of goofy fun activity is great because it gives you both the chance to relax a little, laugh and have some fun.

2 - Perhaps steer the conversation towards more general subject matter - say current events, philosophy, literature, movies, religion, politics. (I know those last two can be a touchy issue with some people, but hey, you're trying to get to know this lady right?) You can learn a lot about a person by the kinds of things they talk about in these given areas, and it helps you avoid the awkward "So tell me more about yourself" line.

3/4 - These really vary from person to person, so it's hard for me to tell you how to gauge it. In general, if the first date went well I'd say a kiss is appropriate at the end.

5 - Walking her to her car is nice. Definitely wait until the 3rd or 4th date to pick her up at her place. When you drop her off, wait until she gets inside before you drive away (I always think this is soooo considerate - whether done by male or female).

6 - The fun stuff idea I kind of already addressed. Perhaps try not to be so structured in your progression of activities. For example, if you've chatted/emailed with a gal already and know she's into art or history, a museum trip followed by coffee would be a fantastic first date. (As a side note, I cannot recommend museum dates enough! Fun, cultural, and always a class act.) Keep your eye on events happening in your area and use those as ideas for dates - concerts, lectures, parties, etc.

7 - The frequency of dates can vary, but I'd say once a week if you're serious about developing a relationship with someone. If you find someone that you know you want to go on a second date with, try to get it lined up for the following week - otherwise they will probably assume you aren't that interested.

8 - Yes! If you really are interested in her, do call/email to keep things going. If you both are genuinely into each other, I'm sure she's probably just as psyched about hearing from you as you are about talking to her. Although, as a general rule, keep communication to every couple days. If you find that your emails/texts/voicemails are being left unreturned, you should probably cool it a little and just wait until you hear from her next.

Good luck, and have fun!!!
posted by bloody_bonnie at 11:32 PM on June 26, 2010 [2 favorites]