Dealing With Valentine’s Day Expectations

Know (and get) what you want this year.

Valentine’s Day is a rough holiday for many people. If you’re single, dealing with Christmas and New Year’s can be painful enough. Maybe you believe that Valentine’s Day is really just a Hallmark holiday. Regardless, it’s hard to ignore the constant slew of cards, candy and advertisements that come right at you after January 1.

We all have expectations for Valentine’s Day. If you are single during this holiday, it’s easy to get jealous. Everyone around you seems to have roses and romance, while you remain single. However, the reality is probably different than what appears on Facebook or TV. It’s easy to get lost in the moment—most of us have seen the pictures of the glamorous wedding of Kim Kardashian and Kris Humphries, and then heard how the marriage fell apart only 72 days later.

Instead of getting anxious, the best way to deal with Valentine’s Day is to face it head on.

If you’re single and know you want to find a date, plan to put time into meeting people for a month beforehand and stick to it! Spend at least 10 hours a week making this goal a reality. Contact friends who might have someone to set you up with and let them know you are looking. Join email lists like Now You Know Events and Cheeky Chicago to hear about what is going on in the city, or visit TCW’s Event Calendar. Instead of hanging out at home during the cold, go out on Friday and Saturday nights—even if it’s 10 degrees below zero. If there are fewer people out, maybe your chances will increase—there’s less competition! By making an effort, you’ll be in a better place than by choosing to do nothing. The upside: You might find a date. The downside: He might not be the man of your dreams, but you still can have a good time.

If you do have a new beau and don’t know what to expect, don’t leave things to chance. Be clear and tell him that you want or don’t want to go out on Valentine’s Day. If he doesn’t respond well to you communicating your feelings, he’s not the right guy for you.

There are so many inexpensive options that can make the day romantic without breaking the bank. Check Yipit or other daily deal sites for a variety of coupons for local activities and restaurants.

If you are single and haven’t found a date, find a friend. Surprise her with a card or gift! The two of you can decide if you want to get manicures, go out to dinner or just rent movies.

Tagged as: love and dating, dating, dating advice and Valentine's Day