Should I buy her sexy lingerie for Valentines Day?

Honestly, this depends on how well you know her. If you’ve been married for any length of time, you already know the answer. You should also know whether she trusts your judgment or wants to pick out her own. If that’s the case, it would be fun to shop together. If that’s hard for you, try it online in the privacy of your home. Just looking around on the net can lead to a pre-Valentines celebration.

If you’re not married, this depends on how well you know her. Sure, you want to get in her pants, but if you’ve never been there, stop and consider how your gift will be received. Unless she's given you some indication that she'd like to take things further, chocolate would be safer. If she has given you those vibes, but you don’t know her well enough to get the right size, then you should consider something like a silky and sheer nightgown, which doesn’t have to be fitted but will get your messsage across.

What size should I buy?

If a) you’ve been together for a long time and b) she has no psychological issues about her size, then just ask. Otherwise, try the stealth approach. Get in her drawers. The one where she keeps her drawers. This is only for you guys who actually live in the same home as the recipient, or else can do it without being caught, such as when you are at her place alone. Maybe you can do it while she’s in the bath, but a shower might not give you enough time. If you are caught, your only good explanation would be the truth. That is, if the truth is that you are going to buy her a gift. Then you’re committed to BUY it.

Jot down the size of her bras and panties. Check more than one of each, since every woman keeps at least one odd size in her underwear collection. You’ll need both the number size and letter size of a bra. Panty sizes are numbers, and have nothing to do with dress size, pants size, or shoe size, so don’t try to extrapolate from other items. Sometimes they have nothing to do with fit, either, since some women prefer to wear panties looser or tighter than neccessary. It’s best to go with the size she prefers to purchase for herself.

While you’re in there, you might take note of her favorite colors or brands. That would be extra thoughtful, but we all know you’ve got something different in mind already. Whatever you do, DON'T make a mess!

If you are buying something that comes in sizes besides bra and/or panty size, ask the sales clerk for help. She can probably guide you by the stats you have. While shopping, try to look vaguely confused. It will get you more sympathetic help than a drooling expression. Please refrain from mentioning whether your recipient is bigger or smaller than the clerk.

What type of lingerie should I buy?

Here’s where the fun begins, especially if you are sure she is open to wearing what you’d like to see. Take a look at The North American Field Guide to Lingerie. This will spell out the difference between a chemise, a teddy, a corset, and all those other things you like, but can’t really describe. You can use this to educate yourself about things to buy for Valentine’s Day, or just look at the models. Either way, definitely NSFW.

As a rule of thumb I just made up, you should probably only go two or three degrees of sexiness beyond what lingerie she already has. Lucky for you, this includes what you bought her last year. If her drawers are full of white cotton bloomers, a silky nightgown might be the limit. If she has thongs and pushup bras already, then you can go for the Frederick’s of Hollywood or Victoria's Secret treatment. If you find latex and leather in her collection, then she doesn’t need your help.

Valentines Day

Keep a smile on your face when you surprise her with your gift, but try not to leer. It will make you look like a dirty old man. When she models the gift for you, that’s the time to go ahead and leer. If you want any action at all, you have to hide your disappointment that she doesn’t look like the model in the catalog. If it doesn’t fit, act like it doesn’t matter. This is important. If she’s overcoming some insecurities to please you by wearing something she would never select for herself, your reaction will determine whether she’ll ever answer your calls again.

Never return lingerie. Even if it doesn’t fit. That’s cheap, embarrassing, and icky. Sure, you can rationalize it by saying she only wore it for a minute, but it’s still icky. The vendor may take it back, but they won’t be able to resell it. If there is a real size problem, just buy another. A lot of that stuff will be half price after Valentines Day. If you can’t take the financial hit, stay within your means... or just give her a box of chocolate.

If you’re really stumped about lingerie for her, try some for yourself! Imagine her face when she sees you in this.

Even if you shop locally, don’t wait til the last minute, because sizes will disappear from available inventory.

I have limited experience in receiving gifts. Some of the previous information came from friends, but I’m sure there are important points that didn’t occur to me because I don’t know all the possible mistakes that can be made. If you have advice, or a horror story (especially a funny one), I’d love to hear it.

The satin chemise in the title picture is avilable at Frederick’s of Hollywood.