Lindsay remembers feeling absolutely delighted when she opened a Christmas gift from her boyfriend to find a beautiful bra.
But her delight soon turned to disbelief when she realized it was two cup sizes too big.
"It was very flattering in that he thought I was much more endowed than I actually was but it was a little bit awkward," says the 29-year-old from Toronto, ON, of the incident that happened a few years ago. "As soon as I saw the tag, I just couldn't stop laughing."
The two had been dating for two years (they've since broken up) and she couldn't believe he had no idea what size she was. She later found out he had gone into the local lingerie store and tried to figure it out by holding up his hands to illustrate and judging from the chest sizes of the sales clerks.
"Anytime you're in the first year or two of a relationship and buying stuff like that, I've always found it pretty damn hard to have any idea what the numbers are," admits the ex-boyfriend.
"I guess I felt a little stupid (when she opened it) but at the same time, how the hell am I supposed to know? I'm sure that happens a lot."
He has definitely learned something from the mishap - he now writes the bra and underwear size of the girl he's dating on a business card, just in case he needs to get them a present.
But many guys are still in the dark when it comes to buying a gift for the lady in their life and find themselves awkwardly staring up at the vast wall of bras wondering what they got themselves in to.
Barbara Captijn, director of Insider Shopping Toronto Ltd., says women need to give their man a little guidance or they can't be disappointed if the gift is off the mark.
"Like everything else in life, I think we have to show men, 'This is what I like and this is what I want,'" says Captijn with a laugh. "Because they are not brought up with that kind of training and I think particularly modern guys must be confused (about) what we want."
Captijn, who started up her personal shopping service business in Toronto two and a half years ago after working in Europe for 20 years, says guys are more sensitive than women might think and they actually try really hard to get a gift their girlfriend or wife will love.
"I really think that's important and they put down some money for it as well so they want to make sure they get it right and I think they get a bit nervous about that."
Captijn recently took a male client shopping to a lingerie store in Toronto's upscale Yorkville neighbourhood and "opened his eyes" to a world of possibilities - everything from elegant sleepwear to crystal-adorned underwear - and since the staff was made up of trained lingerie fitters, he learned a lot.
"It's not just about buying bras. It's like, 'Would we go shopping to buy a jock strap?' There's far more to it than that."
As well as consulting with the sales staff, Captijn says a gift card at a lingerie store is another good option, as long as the guy personalizes the packaging and card to show he's put some thought into it.
If lingerie's not your style, Captijn says there's not a woman she knows who wouldn't love diamond stud earrings or a tennis bracelet, which can be purchased anywhere from The Bay to Tiffany's, depending on your budget.
Experience gifts that the two of you can do together are also great choices, says Captijn, and cites Thai cooking classes and wine appreciation courses as examples.
Or if you really want to splurge, how about airline tickets for a weekend get-away to Montreal or New York? What could be more fun that sipping cappuccinos at a quaint caf� or taking a romantic stroll through Times Square?
And for the other lady in a guy's life - his mother - there are plenty of gift options that don't involve her having to cook or clean to use them.
"Moms are always saying, 'I don't need anything. Don't get me anything,' and that takes the wind out of your sails. But I've never heard of anybody who said 'I wouldn't like some fresh flowers,'" says Captijn.
She suggests pre-paying for six months worth of flowers at the local floral shop, where Mom can go in every month and pick what she likes.
Or since moms are often more concerned with the family than themselves, Captijn says digital picture frame complete with loving photos or a "mom-friendly" camera are also great ideas.
Pampering gifts are always a good choice - anything from spa treatments and aromatherapy massage oils to one of Captijn's shopping excursions, complete with expert fashion advice and a personal limo and chauffeur.
She advises men to walk around a few stores to get some inspiration and really pay attention to what his significant other or mother likes to make the gift as personal as possible - no matter what the budget.
"Even a guy who has money (to buy anything), the woman wants to know that there's something about her that he finds special."
For more information visit www.insidershoppingtoronto.com.
