It’s the Redheads, Charlie Brown! Or, How to Stop Getting Rocks and Start Getting Dates

From this point forward, this column will be a mixture of community-submitted questions and columns based on my own experience. I can also answer short questions without printing them, so submit to

I Think I have Charlie Brown-itis. Swat is filled with countless Little Redheaded girls and I’m too shy/pathetic to approach and if I do I end up making a fool of myself. Since the Doctor seems to be in: Lucy, can you please cure my hesitation/timidness? Each time I try kicking the football I fail. ☹
-The Barber’s Son

(As the question was asked with these genders in place, this column will refer to the asker as male and the asked as female, but this is obviously pretty universal across genders and sexual orientations.)

Of course, TBS. Charlie Brown-itis is the pits.

First off, wearing the same shirt every day is often frowned upon. People like to know that you own more than one set of clothing. And stop asking Lucy for advice. She’s the one keeping the football away from you – and have you seen the way she looks at Schroeder?

Girl has the same problem you do.

But on a more serious note, asking someone out is really about three factors:
1. Appearing not creepy
2. Getting your point across
3. Convincing yourself that the question and the answer are not a big deal

Breaking it down further, the first two notes are about raising your chances of success, and applications of them vary based on the context of your existing relationship with the asked. The third point is really about getting over the nerves associated with asking.

Of course, it’s a week before Screw Your Roommate, so you can also just convince your roommate to do the asking for you.

1. Appearing not creepy

The technique that we used in middle school (or at least, the one that my peers and I used) was generally to approach someone in a very public place, often when the asked is in a large group of her friends, and blurt out “Will you go out with me?” with absolutely no segue into it, and then run away after receiving an answer.

While this is probably the most honest way to ask someone out, as it gets rid of all pretext, it tends to come off as less than cute when performed by people over the age of twelve. To appear less creepy, try creating a situation in which asking your intended out feels more natural. In most situations, this means talking to her about something that is not-asking-her-out before proceeding to ask her out – usually something that you have in common. This can also indicate how popping the date question will go, because you can get a feel for how interested she is in talking to you.

I like to do this while walking somewhere together. Obviously this isn’t necessary, but walking next to someone is less confrontational than facing each other, so it doesn’t feel like as much pressure. Also, if you’re walking in stride, your bodies are already in sync.

If you are asking out a friend, hopefully this isn’t an issue because you have already talked to her, and she doesn’t think of you as a potential serial killer. If you have mutual friends with your intended, you can enlist them to help with engineering, or finding some event the two of you can attend and then talk about. (Full disclosure: this totally worked for me. A friend got a bunch of people together in Kohlberg to watch “It’s a Wonderful Life.” Spencer had never seen it before, so we talked about it for a while afterwards until he asked for my number.) If you’re in a class with her, that’s easy. Talk to her about some aspect of class, and then ask to talk more over a meal.

The hardest predicament is if you have no logical reason for knowing someone – other than that this campus is the size of a postage stamp. This is when you need to create a situation out of thin air in which you can talk to her. It’s possible, but it usually involves a lot of luck and more than a little bit of actually being creepy, because you have to be on the lookout for her in unrelated situations and then try to make small talk with someone you really don’t know. Examples: waiting behind/in front of her in a food line, getting cereal next to her in Sharples, or holding a door open for her. These are also the most tenuous situations because she has the least reason to engage with you, and are usually only successful when combined with some amount of game and/or charisma.

2. Getting your point across

Getting your point across is actually probably harder in college than in any other time in our lives, because the majority of our time is spent either doing work or socializing, often with new people. So, depending on how you ask, it can be hard for the asked to tell whether she is being asked on a date or just asked to hang out as a friend.

This can be cleared up both by wording and your chosen activity. Saying “Would you like to go on a date with me?” is obviously the most clear, but it’s often hard for people who get nervous to ask this because it is blunt and leaves you vulnerable. On the other end of the spectrum, asking someone to go to Sharples with you is often not seen as a date because most people eat at Sharples 2-3 times a day, every day. Usually while socializing with people while not on dates with them.

So it’s really about finding a question in between these two poles that is clear, but that you’re still comfortable asking. I, personally, like to ask someone to dinner and clarify that I would like to cook for him. If you can’t or don’t cook, it might mean asking someone to the movies, or to a restaurant, or to hang out on the playground behind the Quaker Meeting House. Whatever floats your boat.

3. Convincing yourself that the question and the answer are not a big deal

Convincing yourself that the question and the answer are not a big deal is probably the most important step because it makes the other steps easier. This is the same as any other stressful life situation: it becomes impossible if you see it as potentially life-changing.

When you like someone a lot, it is really hard to face the fact that they might turn you down. But as the Fruit Bats say, “When you love somebody and bite your tongue, all you get is a mouthful of blood.” It’s gross, but it gets the point across. When you like someone but you never give her any indication, you will never get anywhere. Being rejected sucks, but in the grand scheme of things, it’s better than pining. If she does like you back, but you never ask, you’ll never know. I like to deal with this by asking a guy out fairly soon after I have realized that I like him, when feelings aren’t as intense and the stakes aren’t as high – but to each his/her own.

The internet told me that a psychological study found that if a crush persists for four straight months, the brain processes it as love, but the internet also appears to be unable to link me to this study, so there’s a high likelihood that it’s a load of BS.

Either way, it still holds true that the longer you wait to ask someone out, the harder it becomes. And in reality, rejection is only as bad as you make it. People feed off each other’s social cues. If you ask someone out and they say no, and you act stupendously awkward for months, she is going to feel awkward or guilty as well, and it’s a miserable situation for everyone. But if you can convincingly pull off nonchalance afterwards, your rejector won’t feel that weird about it and it will become a non-issue pretty quickly, leaving you to move on to greener, more affectionate pastures.

There is no getting around the fact that a lot of dating advice is really straightforward. But even though it sounds like common sense when written down, a lot of it is really difficult in practice. So good luck. I hope that your little red-haired girl becomes your little red-haired girlfriend.

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