Advice on life, love and relationships
E-mail dilemmas to firstname.lastname@example.org
Q: I’ve been dating these two girls casually for a while, and now I don’t know what to do about Valentine’s Day. I know both of them expect me to take them out, but because that isn’t really possible, what do I do? ~A Guy
Chick: Planning two dates on the same night might seem like fun for you, but it could also be hell if your timing is off. Plus, avoiding going out with either of them by coming up with a lame excuse like you’re sick or you “don’t do Valentine’s Day” might not work so well either. Even though you claim you’re dating both these girls casually, I’m sure there’s one of them you’re a little more interested in and that you have a little more fun with. Choose her as your date, go out and have a great time. Understand, though, that because of all the strings attached to Valentine’s Day, the girl you end up taking out might expect things to get a little more serious, and the girl you don’t take out might get annoyed and not understand why you can’t take her out. So choose wisely and be prepared for whatever follows, but also understand that perhaps just dating one girl can be a lot more fun than casually dating two.
Dick: Why not go out with both girls? First thing: Power Bars and water all day. Have a romantic 4 p.m. dinner set up by the waterfront. Take the less attractive one to this date. You can spend two hours there, two hours at your place and be ready for dinner at 9 with the other girl. The water and Power Bars are important because otherwise you won’t be able to last through the night and you will be caught for sure. Preparation will be key; you have to have a good reason to do the early dinner and make sure you keep the names straight. It also is important to make sure that you shower in between because, besides itchy balls, girls can pick up another girl’s perfume and other smells like it is their job. Don’t plan anything the next day – you will either be too tired and satisfied or sore from having one of them beat the snot out of you.
Q: There’s a girl I have a good friends-with-benefits relationship going on, with whom but now that Valentine’s Day is coming up, I’m wondering if she expects me to do something with her. I don’t know how to handle the situation without messing things up. I mean, I’d like to hang out with her and hook up with her this Friday, but I don’t want to give the wrong impression. Then again, I really do like this girl and I don’t want her to think I don’t care by purposefully not making plans. Advice? ~Confused
Chick: You have to decide which way you’re leaning toward, keeping things as they are on a friends-with-benefits basis or open to something a little more. Please don’t do something with this girl on Valentine’s Day if you don’t want your present relationship to change just because you feel that she expects you to. That will give the wrong impression. If the subject comes up, tell her that you’ve already made plans with friends of yours and leave it at that. If you’d like your relationship to evolve into something a little more than consistent hook-ups, ask her what she’d like to do for the 14th. Be honest and say you don’t want to do anything big, but let her know that you’d like to spend time with her and perhaps bring her a few flowers when you meet up, even if it’s just to watch a movie and fool around. Just remember to be honest with yourself first and not feel pressured by her expectations if she’s moving in a direction that you’re not ready for.
Dick: If it crosses your mind as cute or romantic, steer clear, you might as well put your own collar and leash on. Meet her at a bar or something later that night, but don’t do anything that could possibly be conceived as romantic. Drinking is a good option because then you can be affectionate and have an excuse. Also, do not spend money on her because she will read it in two ways, first that you want a relationship or second, that you are buying sex. Either way, you will not be happy with the outcome. As much as you don’t want her to think there is a potential relationship, she will not want to be thought of as a whore. Staying in a friends-with-benefits relationship is harder than getting with your best friend’s little sister and acting like you are interested in the quickest way to a (gasp) monogamous relationship.
Q: My roommate recently broke up with her boyfriend and she’s been really upset ever since. She cries all the time and just mopes around the apartment. Now she wants to spend Valentine’s Day with me, just hanging out and ordering in, but the other day the guy I’ve had a crush on forever finally asked me out to dinner – on the 14th. I don’t want to upset her, but I really want to go out on this date. What do I say so she doesn’t become even more depressed? ~Stuck
Chick: As much as I’m all for the motto “chicks before dicks,” I think that you should definitely go on a date with this guy. Asking for a first date on Valentine’s Day means he likes you a lot, and if you’ve really had a crush on him for forever, this is too good an opportunity to pass up. If your roommate is a good friend, she’ll understand how important this is to you. But if she makes a fuss about you “abandoning” her, then just explain that you’re sorry her heart was broken and that you will be there for her, but you just need this night to see how things go with your crush. Then, either make plans to go to brunch together that Saturday morning, or offer to hang out with her before your big date. Even though she’s miserable, she’ll hopefully understand, but it’s better to let her know sooner than later that you’re busy on the 14th.
Dick: Think about it this way, who is gonna give it up – your whiny, mopey roommate or your hot crush, who is sure to give you a lesson in the horizontal mambo. Your roommate is depressed and that sucks, but if you don’t get out and have a good time, then you will get depressed too, and that’s not good. My suggestion is to think through your ex-boyfriends and guy friends. I’m sure there was one who found your roommate cute that you can set her up with. It sounds like she needs to get some more than a pubescent boy does. The best thing you can do is help her into bed with someone. Sex is the key to making her happy, and any guy who goes out with a girl on Valentine’s Day is going to be expecting to get some, so it will work out perfectly. Either that or rent her a movie, buy her a dildo and go back to his room.