Planning Fun and Fabulous First Dates

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Planning Fun and Fabulous First Datesby Ronnie Joy, The Midlife Dating Coach

Want to try something other than the usual coffee date? Want to upgrade your first date? Do something fun and interesting and have a worthwhile experience – even if he ends up not being second date worthy!

What will you look back on after six months of online dating? Companionship for a series of interesting activities you enjoyed or six months of meeting at coffee shops? Each offers you the chance to meet men, but only one gives you the opportunity of having interesting activities to build good memories on and an optimistic attitude about future dates.

You’ve screened and researched the men. Now it’s time to upgrade your first date!

Choose an interesting activity that you enjoy but might resist doing if you didn’t have a companion.

Offer to “go Dutch.” Freeing the man from paying for everything on your first date can create more activity opportunities.

Offer a choice of two or three activities for the first date. Be flexible to whichever one he wants. Most men will be thrilled that a terrific woman has taken the time and trouble to find something fun to do and then takes the initiative to invite him to join her. Taking this approach separates you from the rest of the dating pool. You’ll establish yourself as a creative, enjoyable companion.

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9 Great Activities for First Dates

Create a list of no less than 9 possible activities for first dates. You’ll always be able to offer your date at least two choices. (Remember: Always meet in a lobby or public area. Arrive and leave separately.)

Use this list as a starting point and edit it to fit your own interests and to match what’s available in your area.


  1. Meet at a bookstore: You can browse the books together and have plenty of conversation topics easily presented to you. If the date is going well, you can consider going to dinner after the bookstore.
  2. Meet in the lobby of a local art museum: Museums have so much to offer and are beautifully designed. You can dress up and look your best. Even if you know very little about art, you can find an exhibit that will stimulate conversation. No advance ticket purchase is required. You can buy tickets when you arrive or go when the museum is free. If you are a museum member, you can attend evening events that are like exclusive parties. Not an art museum fan? Go to a natural history museum or planetarium instead. If you live in a city with a museum for science and technology, these often include user friendly exhibits that you can enjoy with your date.
  3. Meet at a music venue: This is great for a first date if you love music and shy about going into music clubs alone. Find the folk club, jazz club, rock club, blues club or country and western club in your area. Classical music is romantic and going to the symphony is an opportunity for an elegant evening. Most symphony halls are lovely places to meet for the first time. Chamber music concerts are often more intimate settings with less expensive tickets. If you enjoy vocal music, there are many choral performances ranging from church concerts to your local college choir. If you both love to sing, invite him to a sing-a-long! Meet at the lobby or at the front door. Decide ahead of time who will purchase the tickets.
  4. Meet at a local theater for a performance:  You can plan on going to the theater for big Broadway shows or intimate, local theater groups. Meet him in the lobby. If your email and phone exchanges have been promising, you may want to meet for a quick dinner before the show.
  5. Find an event at your local college and meet on campus: Most schools have programs which feature performances. The performances cover a wide range of interests. There are often presentations and lectures which are open to the public. You can learn more about science or travel destinations and receive built in topics for conversation.
  6. Go to a local sporting event: It might seem like a long time to be together for a first date, but if you’re both sport fans, pick a game and figure out who will purchase the tickets. College basketball and football are economical choices and fun. Meet at the sporting arena.
  7. Go to a festival: In the spring or summer you can find street fairs almost every weekend. Events have great food and plenty of free music. Enjoy a brief visit at the festival or linger if your date is going well. Remember to arrive and leave separately.
  8. Go to a wine and cheese tasting: There are so many places to find wine tastings. Perhaps you have a local winery that will do a tour or you can find a club with private tastings. Galleries and wine merchants also host events. There are wine and cheese festivals, often at harvest time at the end of summer. Remember to drink responsibly! If you don’t drink wine, watch for chocolate tastings.
  9. Meet at an antique car show: If this is something you enjoy, mentioning this in your profile will draw men with a similar interest. If cars aren’t your thing, how about boats, airplanes or a ride on an antique train?

I know from experience these 9 activities for first dates are fun and interesting, even when the man isn’t a ‘keeper.’ When the man was interesting, I was grateful. It was easy to pay attention to him and schedule a second date where we could concentrate on getting to know each other. If he wasn’t second date material, I was still grateful to have had a companion to do something enjoyable.  Do your online homework by researching the man’s interests and matching them up with activities you want to do, too.  And while you’re having a good time doing a variety of activities, you are also setting yourself up to meet a wonderful man. You will be able to look back over your dating experiences with pleasure! Contact me for a complimentary dive-into-dating discovery session.

ronnie joyRonnie Joy, The Midlife Dating Coach, is a certified life coach, speaker, radio talk show host and author. It’s her passion to teach midlife singles how to successfully navigate the dating world after a long term marriage or relationship has ended. Find out more about Ronnie Joy and her ‘Have Them at Hello’ and ‘Dating in the Wild’ programs and ‘Dump the Frump’ wardrobe makeovers at and Click Here  to receive her free report, ‘7 Mistakes Midlife Singles Make with Online Dating Profiles (and You’re Probably Making at Least One of Them).’

COMING SOON! September, 2016: Ronnie Joy’s co-authored book, Come Out of Hiding and SHINE. Each heart centered story shares wisdom, encouragement, and practical steps to help you come out of hiding and shine because the world needs you just as you are! Take advantage of the special rates of the first release of this book. Ronnie Joy will send you an email when the book and special rates are released. Fill out the contact form here and mention “SHINE.”

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