So you were dating some guy, and it was wonderful. Over time it became less wonderful, until ultimately you two broke up, and you were upset and confused and disappointed, and you cried about it for days. And then you stopped crying about it most of the time, except maybe very late at night. And then you stopped crying about it at all. And then a number of weeks and months went by, and maybe you even kissed someone new, and you basically got over your ex. Except to think that, if the opportunity ever arose, it would be really great if he could see how happy and pretty you are now, and perhaps he could feel a little bad about what he’s missing.

When this opportunity arises, it’s usually in the form of “let’s get lunch” or “let’s get a drink right after work.” And then you hang out for an hour or two, to prove that you are over each other and that you don’t hate each other. Lunch is usually a good choice for this sort of thing because it’s obviously not a date. It’s not going to wind up with you two accidentally making out again. No one makes out over lunch.

The real question, then, is: What are you going to wear?

You can’t wear the clothes you would wear on a date, because this is not a date. It’s lunch. Plus, you don’t want to look like you obviously put a lot of thought and effort into choosing your outfit for this. That would indicate that you still cared about him, which you don’t, and that you thought he’s worth dressing up for, which he’s not. So set aside your lacy camisoles and kitten heels and eyeliner. That would make him think that you’re still into him, and the entire point of this lunch is to prove that you’re not still into him. Personally, I would advise against even straightening your hair, unless you can sincerely say that you use a flat iron every day. He is not worth singeing a single strand of hair out of your scalp.

Basically, you have to show up looking beautiful, but also like you exerted no effort whatsoever, like you are just naturally this hot, and don’t have to rely on any "tricks" or "expensive cosmetics" to take his breath away. This is not easy. Here are a few ideas:

    •    Wear only slightly more makeup than you would on a normal day. If usually you would wear no makeup to lunch, just put on some mascara and lip gloss. If you wear mascara and powder whenever you leave your house, maybe step it up a small level to include some eyeliner and blush. It’s daylight. Keep it subtle.


    •    Boots are often good. They’re purely functional. Even if they happen to have high heels. They are intended to keep your calves warm, for goodness’ sake.


    •    Well-fitted long-sleeved shirts work wonders, particularly if they are turtlenecks, which give off the message of “I might conceivably be hiding love bites from someone else who you don’t even know about!”


    •    Jeans. Jeans that fit you well. Jeans are easy, casual, classy, and indicate that you would not spend $10 at a drycleaners just to wear something clean when you see him.


    •    Have a new haircut, or wear some adorable headband that he has never seen before. The hope is that he will wonder how much else has changed about you since your break-up, and how many other wonderful new developments in your life he has missed. (Answer: All of them.)


Dressing for an ex-date is perhaps harder than dressing for a first date. But it’s worth it for the moment when he tells you, “Wow, you look great,” and you can reply, “Do I? I didn’t even notice.”