Notice: All forms on this website are temporarily down for maintenance. You will not be able to complete a form to request information or a resource. We apologize for any inconvenience and will reactivate the forms as soon as possible.

‘Tis the Season to Plan an Awesome Date

couple having a winter picnic
It's the holiday season, so you know what time it is: time to finally ask the girl you've had your eye on for the past year on a date.

It’s the holiday season, so you know what time it is: time to finally ask the girl you’ve had your eye on for the past year on a date.

I like it when a guy can put together a fun date, and I think most women would agree. In fact, my worst date was roaming around a mall asking the guy I was with what he wanted to do.

He didn’t know. He didn’t get a second date.

So in the spirit of giving, I’ve done extensive research (asking my roommates and various friends who happen to be women) and have compiled a list of date ideas.

Word of caution, fellas — women are like snowflakes, unique and sparkly, so tweak these ideas as necessary to fit the specifications of the girl you hope to impress.

Cookbook date

This date requires a bit of spontaneity. Go to a local bookstore and peruse the cooking books. You and your date agree to choose a book, flip it open to a random spot and cook the recipe on the first page you open. Be sure to pick a book that fits your appetite and budget.


This idea is for those of you living in warmer climates. Kayaking could be a fun experience for an outdoorsy type of girl — just make sure she doesn’t have a fear of water. If you want to step it up a notch, sign up for an excursion if it’s offered. For example, a lake I’ve kayaked offers guided tours to view waterfalls.

Zoo/aquarium date

Be a big kid for a couple of hours and take your date to the zoo or aquarium. It can be a fun, low pressure way to get to know one another while exploring. Some zoos and aquariums do behind-the-scenes events (such as feeding the animals or getting to see their habitats) so definitely check that out if it’s offered. It would also be cute to ask her to this date in a creative way such as putting clues in an envelope and having her guess where you are taking her.

Dessert picnic

The way to a woman’s (well, mine, anyway) heart is through her stomach, especially when you are feeding her something sweet…preferably chocolate. For this date, pack a couple of her favorite desserts in a picnic basket (or something resembling a picnic basket — presentation is important). Before you decide what to purchase or make, do some research. Ask her friends which desserts she likes. I suggest you pack three or four small desserts to keep up an element of surprise. Take her to a nice park and have a dessert picnic!

Paint and wine class

If you are pursuing a girl who has a creative, artsy side, try taking her on a date to a paint and wine class. Even if your painting ends up resembling a toddler’s art creation, this can be a chance for you both not to take yourself too seriously.

Themed date

A friend of mine told me about a few of her favorite dates, one of which was a Japanese-themed date of sushi and karaoke. Um … genius! I love that idea. So fellas, consider picking a restaurant and activity that corresponds. Think of something like Mexican food followed with salsa dancing, or Italian food followed by a Renaissance art exhibit.

View Christmas lights

Who doesn’t love viewing beautiful Christmas lights? But if you decide to go with this idea, have a plan. Don’t wander around aimlessly “looking” for Christmas lights, as you’re more likely to make your date anxious. Know ahead of time a neighborhood, event or display you can go to. In my city, the zoo puts on a beautiful Christmas display each year. I’ve also seen Christmas lights in a neighborhood that puts on a huge display complete with cookies and hot chocolate. You get bonus points if you bake holiday cookies to bring along as you tour the Christmas lights. Be sure to put the cookies in plasticware or one of those holiday tin containers so they don’t get squished and crumbly.

Well, there you go, fellas. I’ve done half the work, so now all you have to do is ask the girl on a date. Let me know how it goes. Ladies, share below some of the best dates you’ve been on and what made them special. Men, throw us your questions and we’ll do our best to answer creatively and honestly!

Copyright 2022 Tenell Felder. All rights reserved.

Share This Post:

About the Author

Related Content