First Date – What to Talk About

What to talk about on a first date I’ve written before about conversation starters for first dates (see What the Heck Do We Talk About?) but it seems to be something that EVERYONE has trouble with. So here are a few more questions to get the conversation rolling on your first date. Or, if you are using an online dating service, use these during your IM or phone conversations.

The trick is to ask probing, open ended questions. Ask questions that can’t be answered with a quick “Yes” or “No.” It’s also important to ask questions that will touch on subjects that are important to you. Only by really asking and actively listening to the responses will you learn enough about the other person to determine if there is real potential in the relationship.

10 Sure Fire First Date Conversation Questions

  1. How was your day? – Sometimes we get nervous, and we tend to forget the little pleasantries that are part of polite society. Not only is this question a great icebreaker, but their response will give you tons of information. Are they a pessimist or optimist (don’t let one bad day make or break a relationship, ask this question EVERY time.) If they did have a stressful day, you can then keep the conversation more lighthearted and fun.
  2. Do you have any pets? – Pet “parents” love their pets. Some people can’t stand the idea of furry creatures roaming their homes. This is a great chance to find out if you are compatible when it comes to four legged friends.
  3. If you could wake up tomorrow anywhere in the world, where would it be? – I LOVE to travel. I have dated guys who thought going into the next area code was all the world travel they needed. If you have a desire to see the world, this question will help you connect. Also, some people are happy with safe, well known tourist destinations, while others love to get off the beaten path. Even if you both like to travel this will help you discover if your ideas match up on “roughing it” or if you are moving in two different directions.
  4. What has been your favorite vacation so far? – This is a great follow up to the previous question, and will give you an idea of how well traveled they are. It also will let you know what they really enjoyed – was it backpacking or a 5 star resort?
  5. Are your friends mostly men or women? – For me this is a really important question. I like to let guys know that I do have a lot of male friends. I once got to the phone call stage, not even a first date, and the guy threw all this possessive nonsense my way. Guess who never had a first date. It also lets you know who you will be likely to meet in the future, if things go well.
  6. Did you have an imaginary friend when you were young? – Imagination can be important. So can sanity. This is a safer way to bring up childhood with out reminding someone of huge trauma, and it can be a little bit silly. Just be prepared to have your imaginary friends meet!
  7. If you had $1,000 to blow how would you spend it? – Financial responsibility! To some, that’s making responsible investments, to others, that’s knowing where the quarter on the floor of their car is. The trick to this question is that this is supposed to be FUN money – so if your inclination is to pay off bills…well you might want to live a little.
  8. What is the most annoying thing that someone could do to you? – While this one could end up in a gripe fest, pet peeves are important. Learning those things that set the other person off will give you huge insights into their personality.
  9. How do you usually spend Sundays? – This can touch on religion with out being too pushy, and it can also help you determine the activity level of your date. I personally would much rather date someone who likes to relax and rest on a Sunday than someone who wants to be up at 5 am going for a 10 mile run up a mountain.
  10. Are you a morning person, or do you find yourself at your peak later in the day? – Another good follow up question – remember how I feel about that 5 am run? I’m the same the other six days of the week. Not only is this important if you get grumpy when you meet a morning person, but people who have later rhythms will tend to stay up later. I used to work until 9:30 at night, and was dating a guy who worked at 7 am. By the time I got home, he was ready for bed, and our dates never lasted long.

Keep in mind this is not a checklist. You should not rapid fire these questions at your date and note their answers in number 2 pencil. I recommend you think seriously about what YOUR answer to each of these questions would be, and use the questions you are the most comfortable answering as your “fall back” or ice breaker questions. If you can get the conversation flowing, you shouldn’t need to use your whole arsenal at once.

Written by Mandi

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6 Responses to “First Date – What to Talk About”

  1. stormwhistle says:

    Great tips. Thanks for the advice

    stormwhistles last blog post..The Greatest Olympian Of Our Time

  2. Laura says:

    Your point of view is a bit old fashioned. The posts are all about women looking for men to date. How about something for men who want to attract women? I really think it is the men that need serious help, not the women.

    Lauras last blog post..The Mess Meme

  3. the prophet says:

    thanks for the advice!

  4. Mandi says:

    Laura,You do have a good point, so keep reading. Because Kay and I are women, of course, we tend to write from that perspective. We appreciate the feedback, and we actually have several articles in the works that I think will address the imbalance. As to who actually needs more help, that can be a toss up – it depends on what issue! Like I said, keep reading (and guys, you should really subscribe!) because we have some new articles coming out soon. I like to research my topics thoroughly before I post! Thanks so much!Mandi

  5. ebazaar says:

    Well, I think it’s more of direct and important questions rather than old-fashioned. Can be a little scary too for some of the points.
    I’d rather go for something light for starters like ‘How do you do?’ or ‘what do you do in your free time?’, just like appetizers, then the first course and then the main course. It’s the first date, of course you wanna dig what’s important…you wouldn’t want to waste much of your time but bombarding with hard to crack questions can be devastating.
    Well, that’s just my personal opinion though.

  6. Beth says:

    ebazarr – you think asking about pets and vacations is too serious? And if you re-read the article – how are you doing was the lead in question……

    This is a fantastic list – so much better than the boring crap I see on other sites! I will be back for more!

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