Interesting scenarios. Or should we say, sorta weird situations that your girlfriend wants to fit you in. From your email, you told us of three situations that your gf asked you to do. The first one is that she wanted to see you on a lace underwear. She even bought you one. You did not react or said anything when she gave that underwear or even during the time that she presented the idea to you. It's possible that she had interpreted your silence as agreement. I think, it's important for you to really tell her what you think about it, that wearing lace underwear is really not your thing. Be open and honest with her, and then go from there. The second situation, is a little bit awkward, I just don't see any logical reason why she wants you to drop your shorts and show your underwear to her brother. There's that part of you that feel that she's a little bit bored and she wanted to do some kind of practical joke on her older brother. Here's the thing, you know that his brother always has that thing or crush with you, chances are she's also aware of this, so when you think about it on a bigger scale, it's not a good idea to say yes to her, you have to respect and understand the feelings of her brother, and its something that she should also be aware of. You don't want to insult her brother or just simply treat him like he's one big joke. Feelings are serious things, it's not something that you can play practical jokes on. And on the last situation that you told us on your email, you said something about your girlfriend asking you to go to work without any underwear on, it's something that definitely you're not comfortable with because you work for a hotel valet service which means that you're always on the go, comfort is definitely something that you shouldn't be worrying on plus you think that your white shorts uniform will clearly reveal that you're really not wearing anything underneath those shorts, and its something that again you're not comfortable with. I think its really on communication, she's fulfilling a fantasy, and it's something that you need to really sit down with her, so both of you can go over these situations. Let her know how you feel, but at the same time, let her feel that you're always willing to take that extra distance for her, but it should be within reasonable miles. Got Questions? Click Contact. Ask Underwear Click.