Holiday gift guide for singles: The new (but not serious) relationship

Dating around the holidays can be complicated, especially when it comes to presents. A few people have recently asked me how to handle that whole gift giving thing when you are in a new relationship. If you have been on more then a few dates but aren’t really serious it can be a little hard to gage what is appropriate. As a general rule, gifts should fall into one of these categories: something he can eat (not in the sexual category), something he can do (preferably with you in the near future and once again in the non-sexual category) or a gift with some sort of humor (that is of course tasteful and classy).

Treat Him To A Great Comedy Show

Try bye bye liver which shows Fridays and Saturdays at 8:00pm and 10:00pm. Tickets are $20

Cook Him Dinner

Find out his favorite food or cook him your specialty. Try or for great recipes.

How To Be Inappropriate by Daniel Nester

Who can’t laugh at a book dedicated to being inappropriate. Available at for $14.95. If you don’t like this one, there are plenty of others to choose from.

Bake Cookies or Cupcakes

Seems a little Pollyanna-ish, I know. Have a baking party with friends to spice up the fun. Look at for great recipes. Technically, you could buy him cookies or cupcakes as well. Check out Swirlz Cupcakes for some of the best in Chicago.

A Mixed CD For His Travels

No, we aren’t talking about the romantic lovey mixed CD here. Keep it old school with a little Salt-n-Peppa or DJ Jazzy Jeff & The Fresh Prince. Think anything that will be fun and make him laugh. You can even download songs through iTunes or Rhapsody so he can put them on his Mp3 player.

Find A Fun Cookbook

If he enjoys cooking or baking, find him a fun inexpensive cookbook so he can try out some new techniques. Barnes & Noble or Borders both have plenty to choose from. This one is available for $14.95 at If he doesn’t like cooking, try another hobby book.

Offer To Take Him To Dinner

If he generally pays, then offer to take him to dinner. There are tons of great restaurants in the city. Try a place where you can share like Quartino (626 North State Street) Want to find other great places? Try or 

Slang Pint Glass

If the guy can laugh at words like “douchebag“ or “dickweed“, try this pint glass. Available for $8.00 at

Funny Vintage T-Shirt

You have to be careful with clothing. Don’t get him a sweater unless you want him to think of you as his Aunt or Grandma. Find plenty to choose from at, like this one for $18.95.


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