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Dating, Conversation Starters and ‘Wow’ Ideas

Dating can be so fun…..or so ….uummm so dry. A lot of it all depends on the planning, so here are some ideas for success.

Tips for winner dates:

  1. Plan
  2. Plan
  3. Plan
  4. Ok, you got the planning idea, right?
  5. When you ask the girl out, don’t say, what do you want to do. She doesn’t know your budget, nor what in the world you have in mind for time frame, distance, etc. You could ask her to choose between two choices however, such as mini golf and an easy hike.
  6. Let her know what you are doing so she can dress appropriately.
  7. Ask her curfew, or what time she would like to be home. If she lives at home respect her parents rules of curfew. If she lives in an apartment, dorm or alone, ask her what time she would like to be back; she may have an early shift to work in the morning, or homework or other things to finish that night.
  8. Going to dinner is not the best idea for a first date, as it can be expensive. Ice cream and talking is perfect. Short and sweet, long enough to talk and see if you have an interest in each other to further the relationship is great.
  9. With that being said, on of my sons’ always took his first date to dinner. He said it was a sure-fire-hit either way since he got a meal he wanted (took her to a restaurant he liked) so he never felt like it was a total loss.
  10. Let your date know BEFORE the date if you are going to dinner so she knows whether to eat before. My girls would go on a date with the presumption from a comment from the guy that they were going to eat and then they didn’t. Their tummy’s would rumble all night…gggrrrr.
  11. Everyone play nice while on a date. One of my girls had her date tell her how foolish it was for her to pursue the degree she was taking in college. It was a first date, and she wanted to tell him the famous line from ‘Gone With The Wind’, “Frankly My Dear, I Don’t Give A _______” but she’s a lady and ignored him. Later in the evening he told her how much he detested chocolate (what????). So when he took her for ice cream she ordered up a double chocolate fudge, lol. You don’t need to insult or be rude. Dating is to find out if you are compatible. Obviously they weren’t from the get-go, so be kind and find common ground and have a fun time.
  12. Always be a lady (gentleman). One year when my oldest daughter was dating they gave out free passes to a local haunted house. A young man took her to the haunted house and when they arrived they were handed a list of things to find for prizes at the end. They had fun and I think may have even gotten a prize. She was asked out by another young man and she was surprised when she ended up at the same haunted house. She didn’t let on that she had been there, but they won prizes, lol. By the end of October she had been there on several dates, all with different guys. The staff at the haunted house began to question her to seeing her before. She didn’t lie, but just said there are so many girls with dark long hair, it could be anyone. She was coming home with lots of prizes though. She knew it would embarrass the guys who took her, knowing it was free passes and that she had been there – many times by the end now – and it was more important to be kind then anything else. So she played along and had that haunted house memorized by October 31st.

 Dates SHOULD be creative and interesting:

  1. Play Frisbee
  2. Take an easy hike
  3. Driving range, then if they don’t golf it’s not problem, but fun to try to whack the all
  4. Mini golf
  5. Take a board game and munchies to the park
  6. Bowling
  7. Aquarium
  8. Theater – the funny melodrama shows are the best
  9. Free concerts, but a good clean one
  10. Festival that is going on in your area, such as a Greek, German or Swiss for example
  11. Be a tourist for a day and visit somewhere unique or quirky
  12. Ice skating or roller skating – ask your date about this first to make sure they can
  13. Fishing
  14. Go to the zoo
  15. Go to the store and get kites and fly them
  16. Make sidewalk chalk art
  17. Play card games
  18. Movie dates generally are a no-no or should be rare. You can’t talk and get to know each other.
  19. Go Paint-Balling
  20. Go for a nature walk

This list should get you going. The main point is to plan!

Conversation Starters*:
It is so important to have things lined up to talk about, especially to a stranger. It is OK to have silence, but not the entire date….boring. So here’s a few ideas:

  • Have you lived here all your life?
  • What schools have you gone to?
  • How many siblings do you have? Brothers? Sisters?
  • What are you most proud of?
  •  What’s your favorite movie?
  • Favorite movie line?
  • What’s your favorite type of music?
  • Who is your favorite artist?
  • What’s your favorite tv show?
  • If you have $1,000 to do anything with, but had to spend it on YOU, what would you do with it?
  • If you could travel anywhere in the world, where would you go?
  • Have you traveled anywhere? Where?
  • Do you have any pets?
  • Where do you work?
  • What career are you working towards/are you in?
  • What’s the best job you have ever had?

Impression killers

  1. Don’t check your phone – no texting, calling, emailing, etc. You are on a date for heaven’s sake!
  2. Do NOT talk about previous dates
  3. Do NOT talk about previous relationships until you are way down the line in the relationship
  4. Do NOT gossip about anyone, anything, NOTHING!
  5. Do NOT speak critical or rude about anything, NOTHING!
  6. Politics can be a risky subject – tread lightly
  7. Care more about your date than yourself in the conversation
  8. Don’t be late


  • Smile at your date
  • Look at your date
  • Pay attention to your date
  • Don’t talk too much* (the above Conversation Starters are to be used in MODERATION as all things are!). Ask a question and let the conversation flow naturally. You do not need to get through the entire flippin’ list on the first date, ok?!
  • Ask yourself often, does your date seem interested in you? Adjust as needed. You may not be able to fix it, personalities do not always mesh, but sometimes we get so caught up in trying to
  • The Gold Rule says it all:  Treat others as you would like to be treated. Follow this sage advice and it will all be great.

Copyright Carrie Groneman, A Mother’s Shadow, 2015
Recognize a blessing and be a blessing today
For More Posts On This Topic:
A Mother’s Shadow’ a novel by Carrie Groneman (available on Amazon), click HERE
Are We On A Date
To Date or Hang Out?
* Happily Ever After
What Kind Of Friends Do You Have
Dress To Impress
Teen Group Date & Party Ideas
Teen Asking & Dance Etiquette


  • You really have the dating advice down here and wish I would have known you back in my dating days! Happy Friday, Carrie 😉

  • This is great advice, Carrie, and I got some chuckles out of it too! “You do not need to get through the entire flippin’ list on the first date, OK?” Too funny!

  • Carrie,
    This is fantastic. I had a few dates in my past lives that could have used this info. Definately saving this to use in, oh, 10 years. 🙂 Thanks so much for the post.

  • Carrie,
    I love this posts. You are so on the money when you say DON’T ASK What you want to do? I hated that question. It mainly came from my NOW husband. Back then, I would feel so bad about spending his money. Maybe, not so much now. You have so great questions too to ask each other and get to know one another better.
    Thanks for sharing!
    Diane Roark

  • Jess says:

    Such great ideas, again. I wish more “kids” would listen to these, these days! 🙂
    Thanks for joining the Link Up this week! Don’t forget to enter the $5 Starbucks Giftcard Giveaway!

  • Amanda says:

    Some great tips and advice Carrie! Thank you for sharing at Merry Monday!

  • Sherry says:

    Good advice for teens. Thanks for linking up and sharing with us at Funtastic Friday.

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