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I was in H&M the other day to buy my girlfriend underwear. It was accidental. She'd just called and, while chatting, said she really needed some, so I decided to surprise her.

Maybe I hadn't psychologically prepared myself, or maybe I'm just a shy guy about these things, but almost immediately upon walking into the lingerie section of H&M, my body temperature rose ten degrees. At my left was a rack of sheer body suits with pink bows drawing one's eyes to where they already naturally go, and to my right, a rainbow cornucopia of panties covering an entire wall. I started to sweat.

It happened so fast I was unable to take off my jacket for fear of looking like a weird sweaty guy looking at women's underwear. Also, it crossed my mind that I was, in fact, a weird sweaty guy looking at women's underwear. Of course, in a way, aren't we all?

For Valentine's Day this year, I faced the fear, walked into shops and collected tips for all the men out there who want to overcome any lingering lingerie-buying phobias.

Focus on your relationship … with a local store

Ideally, the woman you're buying for will already frequent a store. Find out what it is because they will have her measurements on file. If not, take the initiative and get to know a local lingerie dealer.

Most likely, he or she will even be able to sell you something made within a few kilometres of your home. "I don't do alterations," says Maureen Myers, owner of Nearly Naked in Toronto, "but something good about buying locally is that I can put clients in touch with the designers for minor adjustments. And there have been some women who have had things custom made."

Now there's a sexy and sustainable new meaning for "locavore."

You might know her size, but you might be fooling yourself

"When a man says he knows her size, the first thing I ask is, 'Is that English or French?'" says Shana Tilbrook, owner of Tryst in Toronto. "There's a two-cup size difference between, for instance, an English G and a French G."

I'm sure this is less complicated than calculus, but not by a whole lot. According to Ms. Tilbrook, who has trained bra store employees across Canada for 15 years, there are 200 different sizes of bras and each company's fit is unique. So sneak into your woman's drawer and snag a few different examples from different brands, then let the fitters triangulate the data to accurately assess the area above the underwire.

If it's too late for covert operations, go with something loose-fitting like a chemise or a baby doll.

Don't go basic

According to Ms. Myers, if your honey doesn't own any sexy underwear, it doesn't mean she won't be into it. "A lot of women buy what is utilitarian, what's going to get them through the work day," she says. And although they will venture into lace once they've covered the basics, some never get that far.

However, if you are buying for a "first timer," help ease her into it. "Not all women are comfortable with their body," says John Izzo, vice-president of design and product development of Montreal-based chain La Vie En Rose. "Most have one part they are self-conscious about. ... You should offer lingerie but also give her a cover-up – a kimono, a wrap or a robe made of satin or silk. This will make her feel less vulnerable, because she can decide when to slip it off."

Vintage is in style

Ms. Myers showed me a champagne-coloured vintage nightgown made by Mary Green, a San-Francisco-based designer, which was modelled after one that Ms. Green's mother-in-law had given her. "I have something nice my aunt gave me. Some people pass things down. You know, if it doesn't fit any more," Ms. Myers said, with a wink. While the recycling trend may not have reached the underwear drawer in your household, there's plenty of hot vintage styles in stores right now so you can pretend it has.

Sex doesn't end after kids

I know. Duh. However, I was surprised to hear from Jennifer Klein, owner of Secrets From Your Sister in Toronto, that families frequently come into the shop. "The father will take care of the children while the mother is having a fitting," says Ms. Klein. "They might be tired, but they need to refurbish their relationship a little bit. ... Bringing lingerie into the scene at that point is doing something to appreciate each other." For those extra eager to get back into the swing of things, Ms. Klein even carries a black lace nightie with a snap-on shoulder strap for breast-feeding.

Set the right mood for your gift

"Pretend the bedroom is a stage and the night is a play," says Mr. Izzo. "Make the lighting dim, put on some romantic music and wrap the gift in something pretty and soft. Remember to chill some champagne." Of course, this mood won't turn every lady's crank. La Vie En Rose also offers glow-in-the-dark bras and body paint for the girl who might be less Barry White and more Montreal techno-dance party.

Micah Toub is the author of Growing Up Jung: Coming of Age as the Son of Two Shrinks .

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