Back to All Posts

Ask the Experts: Jessica from Cheeky Chicago answers your “Dining and Dating on a Budget” questions

Whether you’re getting ready for Valentine’s Day, date night or a night out with friends, we’ve got tips and tricks on how to wine and dine on a budget. We partnered with Jessica from Cheeky Chicago for this week’s Ask the Expert series to answer YOUR budget dating and dining questions. Check out her answers out below and be sure to share with us your Valentine’s Day budget date!

Date Ideas

What are some fun cheap winter date ideas? (In summer there are tons of fun free things to do.)

  • Embrace the cold and go ice skating. Make some hot chocolate, bundle up and skate to your heart’s content.
  • Been to any galleries lately? Find out what days are free in your community and hit the art museums or galleries for a fun date.
  • Get physical. If ice skating isn’t your thing, look for free one-time classes at yoga studios, dance studios or even rock-climbing gyms and make a sweat session out of it. Get healthy green juices after and then get cleaned up and rent a movie to watch at home.
  • Truth or Dare. Remember how much fun we used to have playing this game? Snuggle up at home and let the questions or dares begin.
  • Hit the bookstore. Pick out a few of your favorite bookstores in the city and set a budget ($40) so you only get a book or two that you really love.
  • Break out the board games! Fix a cocktail or make some snacks and delve into those favorite board games to bring out your competitive side.


Are budget-friendly dates suitable for a first date or more ideal for “dating” your significant other when you’re already in a relationship?

  • Absolutely. Some of the best first dates are ones where you do “normal” activities that you both enjoy. We can all get swept away with ideas of grandiose romantic dates, but do you really get to know your date on these big adventures? Find out what types of activities your date enjoys and come up with budget-friendly options. Love movies? Maybe find a romantic drive-in instead. Want to do cocktails but can’t spend the cash? Find a local wine tasting. Does your date love French food? Grab a baguette, some fancy cheese and an inexpensive bottle of red wine and go on a picnic. Get creative without breaking the bank – even for that first date.


Any ideas for a budget-friendly night out with friends?

  • While cocktails can be fun, opt for a coffee crawl instead. If the reason you wake up in the morning is to have that first glorious cup of coffee, then a coffee crawl might be for you and your friends. Get your pals together at brunch time and arrange a quick trip to all your favorite cafés. Each of you pick a fave drink and pay for a “round” at your chosen locale. Gorge yourself on breakfast muffins, sinful pastries, lattes and quality girl-time. Much cheaper than cocktails and a lot more fun (just be sure not to OD on caffeine).
  • Look for free events. Lots of art openings and festivals have free or discounted tickets. Peruse what’s happening in your area (this is where our handy Cheeky calendar comes into play) and each take turns planning a fun, inexpensive event to do every week!
  • Hit the comedy club! Look for Improv night, which is often super inexpensive and full of budding comics.
  • Want to have even more fun than going out? Have a spa pajama party at your place instead. Suggest everyone bring over some beauty item and give each other mini-manicures and shoulder massages, then have fun watching movies and making popcorn.


Dining Ideas

What recipes could we cook together that are cheap to make?

  • Pick a grain, a plant-based protein (much cheaper than meat) and a veggie to throw together for an easy, delicious meal. A Mexican bowl with rice, beans, tomatoes and avocado is delicious, or a quick pasta with a fresh sauce, frozen peas and a dash of cheese. Think five ingredients or less and shop local when you can to get the best deals.


Are there any reasonably priced restaurants suitable for dates that you recommend?

  • Sometimes the divey places are the best! In Chicago, hit Tempo for giant egg white omelettes, Hot Doug’s or Superdawg’s for a deliciously famous hot dog or order a few appetizers instead of an entrée at your favorite restaurant. Have cocktails at home beforehand so you don’t get up-charged for drinks. Or think brunch! If dinner leaves you broke, opt for breakfast instead.


Budget Dating

Help! Student loans are attacking my dating life! How does this Cheeky Girl stay social without spending a ton?

  • Think outside of what the “norm” is when it comes to dating. Chicago is a fun place to go out, eat, dance, drink and socialize, but you can get creative too. A Cheeky Card member? Use those perks whenever you can. Look for Groupons or deals on Living Social. There’s always something free happening in the city. By doing a bit of research, you might find new places you never would have discovered otherwise!


Do you have any tips on dating on a budget?

  • Keep abreast of what deals are happening in your area. Wine tastings, exhibits, free concerts… they’re all right here. With spring right around the corner, head to the farmer’s market and break out some of your fresh finds on an impromptu picnic under the trees. Watch sunsets. Hit the zoo. Go on a hike or bike ride. Take advantage of the city.


When is the best day to go out and get the most bang for your buck?

  • Avoid Thursdays, Fridays and Saturdays. Opt for events during weekdays if you can, or even weeknights. Mondays and Tuesdays can be great date nights. Bonus? You will often skip the long lines!


Gifts/Other Dating Ideas

Help me with a V-Day wardrobe on a budget! What are some cute outfits?

  • Use what you have in your closet and think accessories! Chances are you have a LBD. Pair with chunky jewelry, a great coat, a sexy pair of stockings and boots, and you’re good to go. Not into dresses? Break out those skinny jeans. Slip on a pair of heels and a blazer, some pretty earrings, a fancy scarf and a fitted jacket, and you’re ready for date night!


What are some inexpensive gift ideas that are still thoughtful?

  • Post-It notes. Grab a package of post-it notes and write sweet little notes or things you love about your partner and post them all around the house. Or grab a large mason jar and fill it with folded note cards that have your favorite memories together.
  • Gift basket. Grab a cheap basket and fill it with your date’s favorite goodies.
  • Coupon book. Think about what your partner’s biggest gripes are. Do they wish you’d wash the dishes, give them a foot massage or talk more? Make a coupon book with just those coupons so the next time your partner wants a foot massage, she can hand you the coupon.
  • Journal. Grab a moleskin and at the top of each page, ask a question you don’t know about your partner. Leave room so they can ask you questions back.
  • Digital Scavenger Hunt. Send photos to your date’s phone that have “clues” for where to go and what to do. Perhaps the prize is you waiting in some undisclosed location with flowers?
  • GrooveBook. Love photo albums but have all your photos on your phone? For $2.99/month, which INCLUDES shipping and handling, get 100 of your favorite photos printed and shipped to you in an adorable 4×6 album. Even better? Each picture has perforations so they can be pulled from the album and framed.