Do you have a wonderful girlfriend and are wondering what to do with her this Valentine’s Day? Don’t worry, we got you fellas. Hey, Tigers! This is Staff Reporters, Veronica Konarkowski and Melony Howe. We are going to give you guys ideas on what to do and get your significant other for Valentine’s Day. This is coming from a girl’s perspective, so you know you can trust us and our advice. We know you are probably a high school student who is still taking money out of your mom’s pocket or has an underpaying job, so we made sure to give you guys some affordable ideas. We will give inspo for dates, activities, gifts, and popular couple activities that are most enjoyable. We are certain after reading this and taking our advice your girlfriend will be the happiest girl ever and love you unconditionally.
Date ideas
Hope you’re ready to impress your sweetheart with a few of the many date ideas we have planned below. Whether you’re looking for a cozy night in or a nice night out, we have ideas that will blow your girl away. We even offered you Chicago’s best and most popular attractions as well as many locations for various activities.
At-Home Date Ideas:
Idea #1 – Movie Night
- Grab your popcorn and cuddle up with your sweetheart watching romantic movies this Valentine’s Day!
Here are some cute rom-coms:
#1.) 10 Things I Hate About You (an all time favorite)
This movie is an emotional roller coaster so we recommend grabbing some tissues. This movie was based on The Taming of the Shrew and is a teen rom-com that focuses on the relationship between 2 sisters who are struggling to discover themselves and getting used to going out of their comfort zone as they find their true first loves.
#2.) To All The Boys I Have Ever Loved Before
This movie is so heartwarming and lighthearted. I couldn’t imagine a perfect Valentine’s Day without this movie involved. The main character, Lara Jean Covey, is learning what love is all about and finding herself. The movie is filled with adorable moments perfect for sharing with your significant other this holiday.
#3.) A Cinderella Story
Well, this is pretty self-explanatory. I mean who doesn’t love a good Cinderella story movie? This is a classic feel good movie following the tale of Cinderella and ending with the perfect happily ever after! This movie is a great choice for couples who appreciate a good heartwarming story.

Now, we got a bit off track there going into depth about the movies you could watch. I mean, what can I say? There’s nothing like a Valentine’s Day just watching heartfelt rom-coms! But here are some more great ideas for indoor dates.
Idea #2 – Board Games
- Board games are so entertaining and a great way to learn more about each other.
Idea #3 – Painting
- This is a fun activity, especially if you love art while also getting to know each other more.
Idea #4 – Bake
- Baking is so fun! Sweets are delicious and making them is a great way to spend your time! Maybe you could make Valentine’s Day inspired treats for one another.
Idea #5 – A puzzle
- Puzzles are great if you’re looking to spend quality time together. It’s very time consuming and a great way to just hangout, talk, and get to know each other more while working together.
Idea #6 – Trivia Night
- There’s nothing better than a good trivia night. You get to spend time together, get to know each other better, and get to let out some good laughs while pairing up and working together!
Idea #7 – A DIY Project
- If you’re looking for a more unique indoor Valentine’s Day date idea, why not do a DIY project together or even make bracelets for each other? As a guy, making bracelets may sound weird, but your valentine may enjoy it! There’s so many fun indoor things you can do with your sweetheart but you just have to really consider what she is going to like and what will make her happy.
Next, if you’re looking forward to a night out instead, fancy or not, here are some great outside of the house ideas along with a few specific locations that we recommend checking out!
Outside of home date ideas:
Idea #1 – Dinner Date
- Olive Garden, Texas Roadhouse, Longhorn, etc. There is nothing like a date night with good food!
Idea #2 – Arcade
- Dave and Busters, Nickel City, Safari Land, Glow Zone, etc. At these arcades, you can also usually find laser tag, bumper cars, go karts, obstacle courses, and more! All of these places are fun on Valentine’s Day…or any other day!
Idea #3 – Bowling
- Waveland Bowl, Lucky Strike, Lawn Bowl, and so many more bowling alleys are around in various locations. Bowling together is definitely a cute and exciting activity!
Idea #4 – Movie Theater
- AMCs or Cinemarks can be found in many different locations and are usually easily accessible! Most have become really cozy with plenty of food options to explore!
Idea #5 – Escape Room
- The Escape Game Chicago, The Great Escape Room Chicago, Fox in a Box Escape Room, etc. are all options when you’re both feeling up for working together and eager for a challenge!
Idea #6 – Drive-in Movie
- Unfortunately, drive-ins are very hard to find nowadays, but we do happen to know that there are still 2 places left in Chicago, Illinois, to go see a drive-in movie! These are ChiTown Drive In and Rooftop Cinema Club Fulton Market. Bringing a variety of snacks is so fun to plan and enjoy while watching a movie of your choice!
Chicago is a very popular city, especially due to its various attractions. The Bean, Buckingham Fountain, Navy Pier, Lincoln Park Zoo, and the Shedd Aquarium are just a few places that we love!

Gifts

Are you looking to score major brownie points with your sweetheart? Are you sick of just getting your girlfriend (or your valentine that may just be a valentine and not YET a girlfriend) flowers and chocolates year after year? Well, this year it’s time to switch it up and allow yourself into the world of Bae Baskets, a basket filled with the cutest little gifts. If you’re not ready to let go of chocolates or flowers but still want to live in the world of Bae Baskets, well do not worry, you can still include the typical Valentine’s Day favorites in your basket. This basket should be filled with the things she loves most–like a cute little Jellycat or a Lego flower set. I know I’d love it if my Bae Basket had a Jellycat and a Lego flower set! Don’t forget things like accessories, beauty products, brand water bottles, gift cards, treats, or just about anything that is meaningful between the two of you that you can think of. We recommend color coding your basket. For example, for Valentine’s Day, you can follow a red, pink, and white theme. This basket is the perfect way to show your valentine just how thankful you are to have her by your side this Valentine’s Day.
MAJOR PIECE OF ADVICE!!!
Finally, to all of the mature men out there, here is an important piece of advice that we strongly encourage: DO NOT – AND WE MEAN ABSOLUTELY DO NOT – PROPOSE TO YOUR GIRLFRIEND ON VALENTINE’S DAY! Do not squish together your anniversary and Valentine’s into one day! These two days deserve to be celebrated separately every year!

In conclusion, Valentine’s Day is a special occasion that reminds us of the importance of love. It’s a day to express our affection and appreciation for one another. This day should focus on creating meaningful and memorable experiences with your significant other. We hope we provided some good advice on planning activities that cater to your significant other’s interests and preferences. The key is to show genuine effort and consideration, making your partner feel valued and loved.
We hope you all enjoyed our article, and please let us know what you would like for us to discuss next time!
References
- Alexander, A. (n.d.). Valentine’s Day in Chicago: Best Things to Do. Choose Chicago. Retrieved January 30, 2025, from https://www.choosechicago.com/blog/arts-culture-entertainment/things-to-do-valentines-day-in-chicago/