First Dates: Your Questions Answered


Every relationship starts with a first date. Some are better than others, we must admit, but first dates are the gateway that either makes or breaks a connection between two people. Throughout my dating life, I experienced both great and disastrous dates, but one thing I did was learn from them. These dates, good or bad, paved the way to my very own happily ever after. I wanted to share with you some of my pro tips that help to make your first date a memorable one, whether the relationship works out or not.

First Dates: Your Questions Answered

Question: I’m always nervous on a first date, what do I do?

  • If you’re nervous on a first date, take some time to decompress. Take a deep breath and don’t take it so seriously.
  • All you have to worry about on a first date is – 1: are you attracted to them and 2: do you want to see them again. That’s it, that’s all. If yes, go on a second date. If no, or something feels off end it there.

Question: Where should we go on a first date?

  • Essentially, you can go anywhere you like. However, I always suggest a casual first encounter, especially if you meet someone online dating.
  • Coffee dates are great (many studies have demonstrated “warm drink, warm heart” which in turn makes you more comfortable. They’re also a limited time frame which helps if the date isn’t going well. I suggest grabbing a warm drink and going for a walk together (weather permitting) because it diffuses any tension or nervousness and the stuff you see will give you something to speak about.
  • On dinner dates, try not to order messy food OR the most expensive thing on the menu.

Question: Should I be worried about my safety?

  • Although you don’t need to be paranoid about everyone you meet, you still need to take safety measures.
  • Keep dates in a public place and NO home dates. Let a friend know where you’ll be and who you’re with.
  • Remember stranger danger is real, especially with people you met online, even if you feel comfortable with them.

Question: What conversation topics should I bring up?

  • Great conversation is both verbal and nonverbal communication.
  • Make sure to be natural, make good eye contact, smile and sit up straight.
  • Be an active listener and ask open ended relevant questions about what they’re saying.
  • Prepare topics related to your interests and their interests from what you’ve already learned from your interactions with them.
  • Don’t speak about your baggage, exes, don’t enter the pity party, money or make it an interview.
  • Do speak about what you’re passionate about, your experiences, your goals and more about who you are without oversharing.

Question: What should I wear?

  • Be classy, comfortable and proper. No need for cleavage or extravagant clothing.
  • Incorporate a little red to catch the eye.
  • Dress appropriately for whatever you’re doing.

Question: Who should pay?

  • General rule is “whoever invites, pays”.
  • You can split the bill, but if it’s just a coffee or drink it’s nice for one person to pay.
  • Take turns for each date you go on.
  • If you know someone is paying don’t be greedy and order expensive things.

Question: How do I know if they are “the one” for me?

  • Really, you don’t know and can’t know on the first date.
  • Don’t worry about the outcome or where something is going and don’t project your intentions/expectations on someone else.
  • Take things one date at a time and enjoy the process. Letting go and managing your expectations opens you up to a more enjoyable experience and helps you get to know someone in a real way.

Question: Should there be any physical intimacy?

  • Some innocent touch – such as a hug, a hand touch – is fine, but do read the situation before reaching out.
  • If you feel that the situation calls for it, a kiss is OK, but a hug and kiss on the cheek is better.
  • Sex on the first date isn’t the end of the world but it’s better to wait because sex hormones cloud your judgement and you tend to ignore red flags. Also, unless you can emotionally handle casual sex and potentially no call back, don’t do it.

Question: Do first impressions REALLY matter?

  • Yes they do. I won’t lie to you – image matters when dating. You and everyone else see attraction first and everything else second. If you don’t market yourself properly and you don’t make a good first impression you’re likely to miss out on some potentially great dating opportunities.

Question: How soon should I contact them?

  • You can contact them the same or next day with “thank you for a great date I had a good time and look forward to seeing you again” or “thank you for your company but I didn’t feel we were a good match, wishing you the best of luck”. Just don’t seem to needy or desperate in your communications.
  • It isn’t necessary to wait more than a day or two, actually it might work against you.

You can listen to my radio chat about first date onThe Goods with Dahlia Kurtz“.


READERS: What are your top tips for a great first date? What makes a first date a disaster? Share your thoughts & perspective in the comments below!

Your Sister in Dating Bliss,

Single Dating Diva

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  1. I love your advice and things to think about. Since I write guys on how to treat women better, to avoid miscommunication. You are very knowledgeable and love your outlook on first dates. Because now days guys can’t come on to strong, from online dating. Then they fit the online creeper profile, have to make her feel safe. but in making her feel safe, don’t do anything that could be misconstrued. AS if you want her locked in your basement and not the real intentions of you wanting a second date. It’s just staying out of your own head and be real. Love you blog and may look into reposting some of it in the near future. Is seen the form.. Once again loved it.


  2. Great advice. I do most of your suggestions on a first meeting (I don’t call it a date). I am very casual, I meet them at the local mall and we order a soda or whatever and take a walk. If it doesn’t work (and it usually hasn’t for me) then after the meeting I wish them well or wait to see what happens (usually they feel the same about me). Even though that round of online dates didn’t amount to second dates, at least they weren’t miserable experiences.


      • Yeah I think having too high of expectations early on is dangerous and I have done it in the past. Now I am more careful and it’s resulted in higher self esteem because even if they aren’t interested, it’s not just about my looks but many things.


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