Anonymous asked: How do I turn my brother into some lucky lady's LL Bean boyfriend? Right now he's no one's boyfriend for good reason (and I'm not proud. Pretty sure he wears jeans he wore in high school still).

Alright, if you’re intending to She’s All That your brother, I think you should take a step back. I’m going to assume your brother has a sparkling and wonderful personality, and that you think he just needs a little extra help. I would start by asking him, does he want to be someone’s boyfriend? Maybe he doesn’t. That’s fine! If he does, and wants some assistance from you to get out there, certainly your help to pick out a nice outfit for going out on a date could be a nice thing but clothes do not make the man. You’ve got to have an interesting person to talk to underneath those sweaters and flannel otherwise it would be like dating a mannequin.

I have found that many men, even long after high school and college, will cherish outdated/ratty/horrifyingly-old-and-practically-decaying items of clothing or shoes for the simple reason that they do not care to find a replacement for an item they think still has another good 10 years in it. (They are usually wrong–but that is just my opinion.) I have also found, that these guys who have an extreme aversion to picking out something new and facing prices they think are insane (”10 years ago these sneakers cost me $15!” Okay, but you were 17 and they still light up so time for a style refresh, me thinks) and the plethora of choices available in stores and online, they become overwhelmed and opt to keep the same old rather than spend time on something they don’t care all that much about. This is why my real-life-human boyfriend gets 1 LL Bean Signature flannel shirt every year for the holidays. It is not something that he has any interest to choose by himself, but he appreciates the addition when it comes, and very slowly but surely he’s learning things about fit and color and pattern, and the things that he prefers in clothing. (Very slowly.)

So, in sum, I think it’s a very nice gesture to give someone a nice piece of clothing that could help them down the path of starting to refresh their wardrobe, but in the end, don’t tell your brother he’s not going to get a girlfriend because he’s an unstylish loser, because it will be much more helpful to build up his confidence about the things he is good at so that if he’s going out on dates he’s ready to dazzle the ladies with his personality and humor, rather than outfit.