If it makes you feel better, I met my husband by answering his newspaper ad (and, ridiculously, warning him in my response that I only wanted a casual dating relationship. So dating a stranger can work just fine.

I wouldn't plan specific questions -- aim to learn more about your date, like tastes, family background, hopes and dreams. Follow where those answers take you. The mark of really good dates is the easy conversation, meaning you shouldn't have to work too hard at the talking.

I am older and have likely dated LESS, so...I can relate.

I think one really important thing (and I say this as a TALKER myself) is to ask questions and listen more. I try to do that in any social situation in which I hope to shine. It's really hard, as my nature leads me to tap-dance and joke a lot (not literally, thankfully).

So, try to curb your chatty ways, and it will make you seem even MORE charming (as if that were possible!)

...not very well. In fact, the last date I was on I had to be told I was on a date.

meaning you shouldn't have to work too hard at the talking.

Ah, you don't know just how bad at talking I am. Especially small talk.

I think one really important thing (and I say this as a TALKER myself) is to ask questions and listen more.

Yes! This is what I need help with! Especially asking good questions that encourage conversation.

...not very well. In fact, the last date I was on I had to be told I was on a date.

If it makes you feel better, I don't think I've ever (as a dude in a hetero pairing) made the first move. At least not without having to be basically hit about the head with a clue-by-four. It probably doesn't make you feel better, but it illustrates how bad I typically am at reading signals (I only caught on later that night after the first date that she mentioned she was wearing her *favorite* jeans; duh, guy).

Good luck!

My own advice would be worthless, but I have "The Cosmopolitan Guide to Online Dating: A Practical Guide for the Dating Diva" open and it says.

Stories... For inspiration, ask yourself the following questions.

When was the last time you did something embarrassing?

What was the most interesting thing that happened at work this week?

What was the naughtiest thing you did when you were little?

What's the funniest thing that's ever happened to you on a date?

What's the scariest thing you've ever done?

What's the funniest story any of your friends have ever told you?

What's the most interesting/bizarre thing you've read in the news this week?

59 Seconds recommends a "Sharing Game" where you gradually escalate to exchanging more personal information to build a sense of intimacy. The ten questions it suggests as examples

1. Imagine hosting the perfect dinner party. You can invite anyone who has ever lived. Whom would you ask?

2. When did you last talk to yourself?

3. Name two ways in which you consider yourself lucky.

4. Name something that you have always wanted to do and explain why you haven’t done it yet.

5. Imagine that your house or apartment catches fire. You can save only one object. What would it be?

6. Describe one of the happiest days of your life.

7. Imagine that you are going to become a close friend with your date. What is the most important thing for him or her to know about you?

8. Tell your date two things that you really like about him or her.

9. Describe one of the most embarrassing moments in your life.

10. Describe a personal problem, and ask your date’s advice on how best to handle it.

I think our concept of dating is a myth invented by 1950s sitcoms.

That whole "friends first" attitude is a defensive posture that usually only means "I'm not looking for casual sex." So, the best thing to do on a second date is make sure your definition of what is happening matches hers. Be bold. You can't see the fences she's built if you cover your eyes.

I got married instead of dating. It's the opposite of 8 minute dating. I'm on my 3rd (and last) now.

Thanks for those questions, T.E.

I never got around to any online dating (but oh wow the rmless protocol looks great!), so I only have remarks about the in-person part.

I usually tried to arrange dates around some event: a game, a museum exhibit, or maybe a shared interest. Hypothetical example: you start dating someone in your book club; you can always chat about the book or the author or the subject. I'm not usually a big fan of the movie-and-dinner dating template for early dates with someone new, but it's popular because it gives you a built-in topic if you need it.

Asking questions is GREAT. It's hard to get specific about that without giving a set list like those TE gives above*, but I'd say just listen and watch while your date is talking and see which part of her remarks seems to be most interesting to her. One hopes she's doing the same for you, consciously or unconsciously. If not, be sure to answer her questions with verve, too! You're fun and interesting!

Ah, you don't know just how bad at talking I am. Especially small talk.

When we met in person, you were chatty, funny, and easy to talk to. I grant you it's easier to keep that conversational balloon afloat in a group than one-on-one, but remember that there's at least one person you know (and I bet there are DOZENS) who think you're easy to talk to. Let go of the idea that you're not good at it; that idea can be restricting.

*I'm not naysaying those questions, just offering an alternative that springs a little more naturally from the ongoing conversation.

Most of my relationships until my 30s were of the casual fell-into-it kind, which I think was highly generational, but after that point I spent a short time doing some actual 'dating' and found that I really liked it - done right, and with someone you're liking, it's respectful, fun, courtly, pleasant.

I agree with Elsa - make sure you're doing something interesting, something that allows for conversation and reactions, because that fuels the talk. Museum exhibit, ice skating, street fair, food festival, cheese tasting, batting cages, mini golf, flea market, vintage record store you've been wanting to check out, etc. Plan a few hours in which there's some variety - sitting and talking vs. being active and walking around, eating some food as well as looking and exploring - have more than one central activity so you can extend if you want to. Have a backup plan in case the place you are aiming for is mysteriously closed.

I agree with Elsa, you're charming as hell. All you have to do is show sincere interest and ask them a lot of questions. Be ready to offer some tidbits about your likes, dislikes, things you enjoy doing, but don't feel like you have to run the entire conversation. Just react to the situation and surroundings and 'be yourself' (classic mom advice that is actually true).

I don't think a movie is the greatest date because you can't (or shouldn't) talk during it. If you do decide on a movie, take a walk and get ice cream afterward so you can talk about it. I also don't think 'dinner at a restaurant' is always the greatest date because you're face to face and acutely conscious of any moment in which the conversation flags. Go for lunches, street food, and all casual shorter meals that aren't the focus of your evening until you're more serious and comfortable around one another enough to enjoy a languid two-hour meal.

*I'm not naysaying those questions, just offering an alternative that springs a little more naturally from the ongoing conversation.

Oh, it's all welcome. All advice is welcome. A script is nice, but I know from doing enough improv that it's better to have an underlying understanding to go by for when you go off the script.

We're going to the Silence of the Lambs musical for date #2. But I take the advice about the dinner and a movie thing. That's not really my M.O. unless I know someone anyway. I'm definitely going to ask her what she likes to do for fun and go from there, looking for common ground.

"When we met in person, you were chatty, funny, and easy to talk to."

"I agree with Elsa, you're charming as hell."

Y'all gonna make me blush. I assure you, I fake it well. Acting! (Was also probably nervous and therefore chatty.)

Just react to the situation and surroundings and 'be yourself' (classic mom advice that is actually true).

Oh yes, riding this one for all it's worth. I'm ok with myself enough that I don't mind if someone else doesn't like me. That's the advantage of a bit of dating; it's more about looking for a particular fit than trying to fit together with a given person.

That whole "friends first" attitude is a defensive posture that usually only means "I'm not looking for casual sex." So, the best thing to do on a second date is make sure your definition of what is happening matches hers. Be bold. You can't see the fences she's built if you cover your eyes.

Oh man, I so hate making moves and/or reading signals. I think more than anything on a date I'm terrified of being some horrible sexual predator or something (hooray, sensitive 90s man).

Though if I do the whole *yawwwwwn streeeeetch* thing, I'll be pretty sure to play it off as a joke. Does that ever work anyway?

I know from doing enough improv

Oh, then you're halfway there, baby! Just remember: "yes, and..."

Oh, then you're halfway there, baby! Just remember: "yes, and..."

!

So true!

I'm convinced that judicious application of "yes, and..." can improve most aspects of daily life. I use it all the time, ever since I realized my natural inclination is toward "No, and here's why." It's a shift from adversarial to cooperative, and that really helps with dating! Just remember that you're in this with someone else who also wants it to go swimmingly.

Oh man, I so hate making moves and/or reading signals.

It isn't rocket surgery, man. I knew The Fella and I had something happening on our first not-a-date when his foot bumped mine under the table and he left it there, and later when I brushed his hand with mine and he didn't yank it away. Look for stuff like that. It's not an absolute indicator of romantic interest, but even with touchy-touchy people like me, it usually indicates a good comfort level with you.

it's more about looking for a particular fit than trying to fit together with a given person.

Yay! It really is about finding someone who likes you and whom you like. That kind of acceptance and affection is worth any number of "oops, bad fit" dates.

I'm a sucky dater, and look at me now! All of my most successful (e.g. led to meaningful relationships) dates haven't really been dates, but such is life.

I think the best second-date activities are those in which you have something else to talk about that isn't yourself. Minigolf, pool, whatever. Movies are kind of iffy because you're in the dark and not really interacting, but they make good THIRD dates :P You know what would be great, though? RiffTrax Live.

If my first dates were "I like to sing opera and knit" [okay, dude; are you frightened yet?], my second ones were the ones where I talked about my family, my past experiences, whatever. I remember watching someone's adult indoor soccer league and leaning over the barrier to talk about my divorce (wheee!) as he talked about his dad's death; I remember learning how to drive stick and then making out in the basement (okay, that was in high school).

Do something where you don't mind looking a little stupid, and go where the moment takes you. It might be McDonald's; it might be heaven; it might be BOTH!

I never dated and that makes me kind of sad. But on the other hand I won the spouse lottery!

If you find out, please let me know. Online dating doesn't work for me. But then neither does trying to meet people IRL, so I don't know what to do.

That's the advantage of a bit of dating; it's more about looking for a particular fit than trying to fit together with a given person.

Absolutely! And this is what I liked about it. I felt more free and up-front and honest than I'd ever felt in the early phases of the ambiguous friend-progression types of relationships I had ni my 20s. IT's a very clear kind of thing, you're both there for a reason and you know what the reason is, and though you can't know exactly what they're thinking all the time you can be much more philosophical about the outcome, since it's totally about the two of you and what each of you wants, and because you have no other relationship or social network complications riding on whether you hit it off or not.

Oops, I didn't mean that kind of bold, but the talk-everything-(!)-through-over-dessert kind of bold, the verbal equivalent of the arm stretch. By dessert, that fortifying pre-meal cocktail has kicked in. This way, you can relax through the actual meal rather than worrying about deciding when to make the big play.

YAY DATING!!! DATING DATING DATING!
It can be so much fun!
You get to meet so many new people and then judge them!

First of all, Eid, good job on creating such a great OKC profile that shows off your personality well enough to be attracting these dates.
Second of all, good job on the communication that leads to the dates.
Third of all, good job on the first date and congrats on finding someone who you want to go out with again and who wants to go out with you again too!

Honestly, you've done all the tough stuff already. Finding someone who you want to date who wants to date you back is (imo) the hardest part. Then after that, it is all about figuring out if you work well together. Of course, you have to be normal enough on your dates to let your real self show through. Other than that, it's really just letting it unfold.

What's that you say?
Not good enough?
Time for round 2?

RMLESS PROTOCOL FOR GOING ON ALL THOSE DATES YOU GOT ONLINE, YOU STUD

First date: (I know you did this one already but maybe this will help in the future)
The goal of the first date is to learn more about each other and not get wasted and not be all awkward and scare them off. The first date shouldn't be too long and shouldn't be late at night. There should be some sort of "activity" but not one that takes all your concentration or takes away your ability to talk to each other (i.e. movie).
Go somewhere you feel comfortable. This doesn't mean that you need to go to a place you've already been to, but make sure the experience is something you can do. Like, I might suggest going to some tiny taco place in east brooklyn that neither of us have ever tried, but you bet your ass I am going to hopstop that shit beforehand and get a layout of the neighborhood, and read up online on what the good things to order there are and what all the words on the menu mean. You don't want to be totally out of your element and paralyzed because of your setting before you even get to talking to the person.

If you like them and things are going well, tell them during the date that you want to see them again and make plans. Suggest something specific (either the event or the day). If your date likes you back, they will either say yes to those plans or change them to another specific plan if they can't do that date. If your date isn't that into it or you aren't that into it and someone brings up future plans, the polite response is something along the lines of "sounds like fun, let's see what our plans look like and figure it out later."
(Later, if you want, you can send the thanks but no thanks email or just let it die.)

(Controversial and disagree if you want) If on a het date, M pays and F offers but M says "don't worry about it, you can get the next date" or "let's go get ice cream after and you can get that" if he likes her or "it's on me" if not. If M is very very poor, he can let F pay for drinks or for the tip. All of this goes out the window if F is insistent on splitting or paying or whatevs.
If on gay date, original asker pays and all of the rest of the above apply.

End of date 1: this all depends on how things go and who you are with. I am a fan of offering to walk someone home and a no-expectations hug at the doorstep. However, I am also annoyingly efficient so I know that if you walking me home means that you will be going 6 blocks out of your way or that you have to go the opposite direction on the subway altogether, I might say no even if I like you. So don't take the response to this offer to mean anything.
Both of you are going to be nervous all night about the end of the date, so basically put everyone at ease by either 1) go in for the kiss during the date and not after or 2) take the whole thing off the table by doing that diagonal-hug-lean-thing so it's clear you're not going for face.
You should agree to go on a second date if you are unsure or if you know you like the person. If you can't ever see it working, then you say no to a second date.

SECOND DATE: Cool, another!
Second dates are for making sure you have a connection and that you weren't just in a hormone haze on the first date or something.
Second dates should be longer than the first date and ideally be two-parters (like a show and then drinks or coffee and then a book reading). You want one part of the date to have an experience together and the other part to talk to each other.
For my second date with my bf, we went to a godawful short film screening then drinks. The event doesn't have to be good, and you might bond more if it isn't. Second dates are the time to go to something stupid that you've been meaning to try.
Figure out what your date likes to eat and drink on this date.

Second dates are also for kissing! If you didn't kiss on the first date, and you still feel the chemistry on the second date, just interrupt whatever you're doing, grab their arm, say something inconsequential like "hey-" and pull them in for a kiss. Again, best to get this out of the way mid-date so you can relax for the rest of it or know that you should excuse yourself if your date wasn't into it.

End of second date: secure yourself a weekend night for the next date. Don't go upstairs but feel free to kiss on the street.

THIRD DATE: this is going really well! Third dates are for getting closer, in both conversation and physicality. Is that a word? Sure.
Schedule the third date for somewhere in your neighborhood. Now you are a local expert. Maybe you even know people on the street and they wave to you and you look cool. Walk around with your date and show them the places you like to go. Take them to a good restaurant or bar or whatever near your place.
Do they want to come see your place after? It's right around the corner, you know...
Of course they do!
Remember on the second date how you asked about their eating and drinking preferences? Well, you just happen to have {berry wine coolers/a bottle of scotch you haven't tried yet/red wine} at home which you tell them. Take them on a house tour, then seat them in the living room (bedroom is too forward) and get them that drink.
MAKEOUT TIME
"You're so good-looking!"
MAKEOUT TIME
"You're so much fun!"
Say nice things during makeout time and say thank you and smile if they are said to you.

End of third date: Invite them to stay over but don't pressure them. If they want to/need to go home, offer to call and pay for a cab or at least walk them to the subway. Tell them you had fun and that you will call them.

Call them.

DATE FOUR: Fourth dates are for compatibility. You should feel more comfortable with your date now, and you know you have chemistry. So now it's about all those intangibles like if you are going to be able to deal with how early they get up or if they are going to freak out when they hear how many toenails you've lost.
Fourth dates should be talking/dinner-centric. Time to go somewhere nice! Tell funny stories about growing up and reveal more of your quirks.

End of date four: sleepover time!

DATE FIVE: almost an item
This might be a good time to meet up with friends or go to some sort of thing you haven't been to before like a concert, and make sure your date doesn't dissolve in public. I was the friend meeting a guy's new gf and she had a total meltdown and literally ran down the street away from us because she got spooked by the crowd in front of a restaurant. See if that happens.

Date Six: this is the "make it or break it" date
Do you want to be a couple? Survive this date and you will be. After sixish dates is when you should start talking exclusivity, if you are feeling that. Make sure that you do the thing where you spend the night and part of the next day together at some point so you know what they are like without having put on their best face for you.

NOW YOU ARE AN ITEM! Go carve your initials in some trees, or break up later or whatever.

Throw over shoulder. Drag back to cave.

Offer to buy/kill breakfast in morning.

Wow, rmless, in awe as always!

I'll go with jonmc's version instead.

I'll go with jonmc's version instead.

Oh sure, NOW you tell me. *sets time machine for last fall*

I am exactly this charming.

Throw over shoulder. Drag back to cave.
Offer to buy/kill breakfast in the morning.

You see why I married that man.

Silence of the Lambs musical? Hmm... cause nothing says romance like singing serial killers. ;

; )

(oops)

I just want to tell you both: good luck. We're all counting on you.

I'm another never dated person, for the record. I just sort of skim through life, with some sort of effability filter on, and if threshold is reached, well then. The threshold is rarely reached.

So much to say sorry can't help, but good luck son, we are pulling for you!

My boyfriend just let me know that the musical is returning to Off Broadway. Is it worth seeing? Also, third date yet?