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Dating (and Friend-Making) Etiquette Points

January 17, 2011
Man and woman flirting in bar, dating, picking up women

Him: Wanna do something later tonight? Her: Really? You don't have a plan AND you're assuming that I don't have plans?

As promised Friday and alluded to intensely on Thursday I have some etiquette pointers for you.

First, I have to state that these ideas are specifically for forming and strengthening new or burgeoning relationships. Relationships that are already deep and tightly formed have a different set of conventions and usually have a lot more variables – and therefore variations – within them. For the most part, while establishing a deep, long-term relationship you usually set up rules between the people involved and then renegotiate them as needed (whether you realize this is what you are doing or not).

But, if you don’t have a relationship established and you would like to try to set one up try to be polite. Here are a few ways to do this:


So, you’ve met someone new that you would like to get to know better. Maybe it’s someone you’d like to get romantic with (or just sexy with). Maybe you are just shopping for a best friend. Or perhaps you are a young lady about town and you need a gay boyfriend to help you navigate modern life. No matter what the situation or who you are trying to get closer to you probably want to hang out with your prospective friend. (When in doubt, chase the girl — remember guys?)

There are a lot of things you can do, places you can go and ways you can arrange spending time together. But at the very least you owe the other person the respect of planning ahead and asking him or her well in advance of the day you want to hang out. I’d say from a week to three days beforehand is a good rule of thumb. But honestly, asking someone on Wednesday to go out with you on Friday is kind of rude because it implies that you assume he/she will not have any plans and it asserts that you already think you are more important than anything this person may have been planning.

I have also run into a lot of situations wherein people will ask the day of (or even the hour of) the event. This is incredibly rude. Think about it. You may think you are being casual, laid back and/or spontaneous, but you are really telling the other person that he or she is the equivalent of an after thought and that his or her time isn’t as important as yours.

The last guy who tried to date my sister did this. I think he really liked her and I think he really wanted to get to know her, but he couldn’t muster up the cojones to put himself out there and ask her on a real date. He didn’t live in the same city as her but he visited her town almost ever weekend. But he never let her know when he was coming to town. Instead, he would call her when he was downtown at the bar and ask her to join him and his friends. Or he would call her on a Friday morning to tell her he was in town and ask if she wanted to have lunch. (Not dinner, lunch.)

She never went on a date with him. Why? Because he was always asking at the last minute and she was usually busy. When she wasn’t busy she was too offended.

There is a friend variation of this that I have run into a lot that I also find very offensive. Here’s the scenario:

It’s 3 p.m. and your work friend comes up to your desk to say hi and to asks you what you’re doing tonight. You say “nothing” because it’s a Monday night and laundry is what you will be doing. “Great, I’ll pick you up at 7 and we can go out to dinner and to the movies.”

No, I don’t think you understand. When I say I’m doing “nothing”, what I mean is that’s my plan. I plan to do nothing. But thanks for assuming that you life is important enough to supersede my need for clean clothes and a “Dancing with the Stars”/”Castle” fix.

It’s like a trick question too because if the friend had said, “Do you want to go out to dinner and catch a movie tonight?” I could have said, “Sorry, I would like to, but I need to do laundry tonight.” But now if I say, “No, thanks,” the friend busts out with a quick, “But you said you aren’t doing anything.” It’s a trap with a planned guilt trip as the jaw to clap down on your head. Don’t take the bait. And for goodness sake don’t be the friend who sets the trap.

Show people the respect of giving them a few days of advance notice and actually make plans with them. It’s the courteous thing to do.


We’re grown ups now. (At least I think most of the people reading this are adults.) We have grown up jobs and that means the responsible thing to do is to go to bed at a decent hour and wake up in time to make it to work in the morning. That means if you are asking someone to spend time with you you should make the plans for early in the evening. Depending on your part of the country this will vary. It will also vary depending on the day of the week you want to hang out, but for the most part on a first date or a first hang expect to meet up after 5 p.m. and before 7:30 p.m. so that you can end the meeting by 10.

Now that’s on weeknights. Weekends are a bit more flexible, but it is rude to expect someone to burn the midnight oil with you when you barely know one another. Don’t assume you can wait until 10 p.m. to go out. For me (and I imagine a lot of other grown-ups) by 7 p.m. I am usually doing whatever I’m going to be doing for the night. That means if I’m on my couch it’s going to be painful to get off of it. Whereas, if I’m out having fun with a new friend I’m good to hang out for a while.

To be fair some people are night owls or work in the evenings and need to hang out during the day. The most important thing here is to take the other person’s time into consideration and don’t assume that he/she has a similar schedule to yours.

Also, in most cases the latter the hour the more intimate the suggestion. Drinks after work mean one thing. Drinks after 10 p.m. mean something else, and the latter is way too presumptuous if it’s a first date.

Have a SPECIFIC Plan

I’ve written a whole blog in the past full of date ideas, and I think I expressed the fact that if you are asking someone to dinner you should be specific about when and where.

“Hey, can I take you out to dinner on Friday night? I was thinking Applebee’s at around 7. I can pick you up unless you’d like to meet there.”

Easy, right? It would seem, but so many people leave out all the details. And that is RUDE.

I know there are a lot of folks out there who are afraid that if they don’t come up with an amazing plan they will get turned down. But for the most part, if a person really wants to spend time with you he or she will adjust the plan from there. But it is rude to just suggest dinner and then make the other person make the plans, or to say, “We should go out” and then expect the other person to follow up. It is overly familiar and disrespectful. If you want to spend time with a person your attitude should be that you would like to show him or her a good time. Make a plan and be SPECIFIC.

Let the Other Person Know the Plan WHEN YOU ASK

As I said, if you are asking someone to spend time with you in the hopes of establishing a relationship it is a good idea to offer a social activity for the two of you to engage in – and to be specific. Doing this will help establish and manage expectations for the interaction.

For example, say I want to be friends with the new girl at work and I know she is new in town. So I invite her to go to drinks and karaoke with me and my friends, and I let her know that I want to introduce her to some people. That way she knows that she doesn’t have to entertain me or pay a lot of attention to me while we hang out because I expect her to be mingling with other people.

On the other hand, if I ask the guy in pre-press if he would like to get a drink with me so that we can “get to know each other,” I have set up a situation within which we are meant to interact rather intimately with one another – not with a large group.

If you said something vague like, “let’s get drinks” to either of the aforementioned folks she and he would not know what to expect or what you intentions for the interaction are. Thus, leaving things open to many different interpretations and a lot of possible awkwardness. What if the new girl at work is gay and she thinks you are asking her on a date? Or if the guy in pre-press is married and he thinks you’re asking him out for drinks with a group of people when you are really asking him on a date?

That’s right, awkward.


My mom used this assumption a lot during my fledgling years of dating — “If he asked, he’s going to pay” — and, sadly, it caused me a few embarrassing moments in my teen years. But I think her advice is sound: If you ask some one out, especially for the first time, be willing to pay. (Of course if you aren’t willing to pay make it clear what you are planning.)

For me this one applies even within my established friendships. If I ask Kendra to go to the movies with me, I will often buy her ticket. (And she is usually sweet enough to but a soda for us to share.) If you are asking a new friend to do something, be willing to pay and let the person know that you are planning on it.

For example, when I asked Daniel to go to the play with me I told him that I had tickets for both of us; so that he didn’t need to wonder if he would have to pay for his seat or even both of our seats. And he was kind enough to ask if he could buy me dinner before the play. That’s the phrase he used. He said, “I’d like to buy you dinner. Olive Garden is near the theatre. How would you like that?”

It’s a simple thing, but so many people leave the details out. And the truth is, if he had just said, “do you want to go to dinner before the play?” I would not have known that he wanted me to consider the evening a date and I would not have known that he intended to pay (which may have caused me to decline because he wanted to go to an expensive restaurant.

Now, if you are planning on going dutch there are ways to let the other person know that. For example, when asking my friend Janet to dinner I have said something to the effect of, “How about Chili’s? That isn’t too expensive for you is it?”

16 Comments leave one →
  1. Keep Your Woman permalink
    January 17, 2011 12:38 pm

    I think one thing many people (men and women) can to to make the entire dating experience better (which is funny because I just posted on this) is to remove the pressure/expectations of that “first date,” or even asking for it by simply making it less informal (for the time being). It gives the two individuals a chance to talk and get to know each other, rather than jumping into a full blown traditional date (only to be let down if it fizzles)…


  2. Logan permalink
    January 17, 2011 1:47 pm

    This blog was uncanny in its timing. I happen to have experienced some bad social etiquette just yesterday, only my situation was on the reverse side of the coin. Flakiness.

    There’s a person I’ve known for about a year now that I’ve been trying to get to know better. Last summer she made me aware of an event happening this weekend, so over a week ago I asked if she’d like to go. Though she seemed to dodge my specific questions about the time of day we’d meet, she agreed to go and even seemed a little excited. I told her I’d contact her a few days before the event to pin down a time. First I called with no answer. The next day ( the day before the event) I texted her. After exchanging a few texts over the course of several hours, she let me know that she might be making other plans. Then late that night she confirms that she has. All of this dodging leads me to believe that she never really intended to go in the first place. Which in turn makes me ask, “Why in the hell didn’t you just say no when I first asked instead of stringing me along?” Much easier in my mind. Also, this is not the first time she’s done this. Flaky people are annoying.


    • January 17, 2011 2:11 pm

      “Why in the hell didn’t you just say no when I first asked instead of stringing me along?”

      Perfect question in this situation…and there are actually a lot of reasons a person might do this. I don’t think any of them are good, but they exist. I’m so sorry Logan. Of all my friends you are one of the most dependable — especially when it comes to making plans to meet up. You totally deserve someone who will give you the same respect. I think the kind of behavior you described is really just extremely self-centered.

      Part of it is a problem in our culture that I refer to as the BBD — the bigger better deal. (I wrote briefly on this a few years ago: She may have been okay with the idea of hanging out with you, but she was hoping for a “bigger, better deal” to come along. (So she is probably stupid cause you are the biggest best deal in so many ways.) So, you were probably her effectual back-up plan.

      I have friends who do this to me a lot. I don’t think they even know they are doing it, but they miss out on a good time with me because they are looking for something they perceive as being better than our plans. I think a lot of people in America today miss out on some of the best people and experiences in life because of their Burger King mentality (My way, right away).

      Sorry man. But I’d like to think you’re better off. Why are you surrounded by stupid female dating options and I’m surrounded by stupid male dating options?


      • Logan permalink
        January 17, 2011 4:30 pm

        Thanks for the insight Crystal. I’m really not surrounded by female dating options, just this one for the moment. But she draws me in like a bee to nectar. That said, I won’t be making any plans to hang out with her after this her third flake out, unless she is the one trying to put things into motion.


        • January 17, 2011 4:34 pm

          Nectar, eh? Wow, that sounds good. Too bad. I have a bit of a third strike policy myself. Although I do try to let people know when they are up to bat and that they are on their last strike. (I TRY.)


  3. jesswords10 permalink
    January 17, 2011 2:17 pm

    When in doubt, chase the girl. Made me chuckle, but it’s all great advice!


  4. January 17, 2011 10:00 pm

    Good tip on the “be WILLING to pay.” I KNOW I need to do this more…. I often invite people out, and then sort of assume they will pay for themselves. This is because I’m cheap 🙂 But, it’s a great gesture and I think is the proper way to go, etiquette wise. Great post!


    • January 19, 2011 8:49 pm

      With tight pals I do like to pay from time to time. But I don’t do it so often that they expect it every time I ask them out. But with my besties sometimes I’ll have an idea and they are hoonest with me and tell me they can’t afford it. And I get to offer to take them out. It’s nice. I actually like to pay and give them something from time to time and I know they like it. Although a couple of them feel a little guilty sometimes. And I just tell them that “If I didn’t want to pay I wouldn’t offer!” Problem solved.


  5. January 18, 2011 6:49 pm

    Hey Crystal, thanks for those book recommendations. I have already read the Non-Designer’s Design Book and thoroughly enjoyed it. I’ll check out the Mac is not a Typewriter. Sounds interesting.


    • January 18, 2011 9:17 pm

      Woo Hoo! I use thoe books to help train my design newbies — I hope you like what you find. If you are interested in newspaper (or brochure or newsletter) design at all Tim Harrower is kind of a god in that realm. I make my news-designers memorize that stuff. Advertising design might be useful to look into for your work. And honestly anything on typography and type layout and design could probably be applicable. I hope your presentations all go GREAT!


  6. January 18, 2011 8:27 pm

    Wow, you offer great advice here! You have made parenting so easy with this all laid out for my young four young adult children. Bravo! I’ll be sending this in their emails along with a mommy recommendation memo.


    • January 18, 2011 9:14 pm

      Wow…I am so glad to be of assistance. I have to say my parents are partially responsible for this list too–they have helped me navigate social waters and taught me some important guidelines. I hope this can open up a great dialogue with you and your kiddos! And thank you so much for reading!


  7. July 1, 2011 5:40 pm

    I’m sure a lot of people don’t know HOW to date these days. Thanks for sharing your information as it seems very practical and thoughtful as well. I’ ve had the misfortune to come across a few “rookie” daters and am not so skillful myself. In the end, it boils down to courtesy and common sense, which I’m afraid the younger generation haven’t the first clue about, and am not convinced they care to know. Fortunately, there are more than one fish to choose from.
    One thing I am convinced of, is that if a potential date can’t follow a few simple rules in the beginning, there isn’t much of a chance that they will learn to.


    • July 2, 2011 11:46 am

      Hey MO…thanks for sharing. And thanks for reading. Lately I’ve been wondering what types of litmus tests are good for the beginning of relationships because I always seem to give people too much benefit when there is doubt. Mayeb I’ll write a blog about that soon. Thanks again!



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