How to Choose the Right Gift for the Person You’re Dating

By: Simone Paget |

Years ago when I was living in Toronto, Canada, I was dating this guy that I was head over heels crazy about. Midway through our courtship he was scheduled to go on a vacation to Britain. Before he left, he promised me that he would bring me back something from his trip. I was hoping for something quintessentially British like one of those cute shopping bags from Harrods or an item from Top Shop (something at the time that we were not able to get in Canada) Instead, when he returned he said, “I got this for you!” and handed me a miniature wooden Totem Pole that you can easily buy in most tourist gift shops in Toronto. I asked him:

“Where did you manage to find this in London?”

To which he replied:

“I found this great store that specializes in items from Canada! I know your hometown is known for its Totem Poles so when I saw this, I immediately thought of you!”

I thought it was an odd gift however, I was in love with him so I let it slide.  A few months later our relationship ended in a bitter break-up for unrelated reasons.

I forgot about his gift until a few years later I was in the Toronto Airport waiting for a flight and noticed one of the gift shops had a huge display of miniature Totem Poles just like the one he had given me. Suddenly a light went off:

“Omg, he totally forgot about me during his trip and bought the gift at the airport before I picked him up!”

I can’t believe I never thought of this before!  The airport Totem Pole has gone down in history as one of the most hilariously bad gifts I’ve ever received from a boyfriend.

So that you don’t make the same mistake as this guy did, here’s a few guidelines for buying gifts for the person you’re dating:

If you’ve just started dating: 

Keep things simple and go with something small and thoughtful like….

  • A nice note or card telling the person that you like them.
  • A book that you’ve noticed they’re been eyeing
  • a USB key with a bunch of songs that you know they’d like
  • small accessory or item that reminds you of them (no Totem Poles please!)
  • Flowers

If you’ve been together for quite some time & things are serious:

You can usually never go wrong with jewelry, shoes, that designer bag she’s been eyeing or a nice piece of lingerie  – just keep it classy and get someone at the store to help you pick out the item before you buy!

You should never give a woman: 

  • Lingerie when you don’t know her very well
  • A self help book
  • Teddy bears or stuffed animals (so not sexy)
  • Anything that used to belong to an ex
  • A USB key full of Michael Bolton songs (unless she’s into that)
  • Men’s cologne (This actually happened to me once. I get that you want me to smell good but, REALLY?!)
  • Anything from an airport gift shop in her home country (& then lie to her about it’s origins)

Did I miss anything? What do you think are good/bad gifts?