sophie
Break My Heart
Yeah, this; I'm worried he's going to take the wrong message away from this experience. Which is to say:
DO: use your words and ask a girl out if you like her.
DON'T: mope around ignoring a girl for 4 months and then give up when she starts giving you the cold shoulder.
DO: create a friendly flirty relationship with someone before making your move. I wouldn't say "dating your friends" is exactly the correct way to do it, but "dating your acquaintances" is.
DON'T: play a long game of establishing yourself as nothing more than a friend (or from the sounds of it in this case, an occasional acquaintance) for months on end without giving her ANY indication whatsoever that you were in any way interested in her.
DO: learn that rejection is going to happen. It's a part of life, and I know, it sucks. But really that suckiness comes from spending months on end building it up in your mind. By spending all this time wondering how she feels about you and not knowing you're building an anticipation up in your mind. You REALLY want this thing; you NEED it; you will be deeply hurt if it doesn't happen. This creates a vicious cycle: the more you build it up, the harder it is to work up the courage to ask her out, the less likely it is to happen in reality.
What's more the whole avoiding asking her out creates a further problem. The problem of "would this actually be a good fit for me?" I would say the biggest problem young guys make when they're just starting to get into dating is they never ask themselves this question. They fixate on the first girl who smiles demurely at them and pursue her to the ends of the Earth without really considering who she is as a person, whether they are in a right state of mind to even be in a relationship, or if they're at all compatible beyond physical attraction. So you pursue this girl. You get her. Great! You last for four months before realizing you guys have nothing in common: you love baseball and cartoons and Halo and she thinks sports are a stupid waste of time, cartoons are for kids and manbabies, and she's never held a controller in her life! Meanwhile she loves Catcher in the Rye, camping, and the Bachelor, and you find Salinger a pretentious buffoon, think sitting in a tent cold and miserable and without the modern amenities is an affront to all those forebears who had no choice but to do so, and find sappy reality TV shows a pointless waste of time.
Now I'm not saying make a side-by-side list collated from everything you can find out about her on facebook and try to make an logical, robotic decision about whether you are X% of a match which falls above some threshold of acceptable compatibility. I'm saying have some actual goddamn conversations with her. Find out what she's like, what her interests are and if she has anything in common with you. Hey, you know what's a REALLY good way to do that? Asking her if she'd like to go grab some coffee or a meal with you sometime in a 1-on-1 setting that allows you to really get a feel for each other and figure out if you work in any sort of a non-fantasyland.
That's what dating's all about, really. It's about interacting with someone you know on a really casual level and trying to get a sense for whether or not you'd work on a romantic level. The biggest error you can make is fixating on one person and convincing yourself that that person is the one and only person for you - that the first date is some dramatic first day of the rest of your lives together, that once you get over that first terrifying hurdle of *gasp* telling a girl how you feel everything else is ezpz.
It's not! You know nothing about this girl! This isn't some sick game of trick a girl into liking me by ticking boxes x, y, and z; this is a you trying to figure out if this girl is good for you. And if you find out she isn't (whether that be because she's not attracted to you and said no when you asked her out, or because on date #3 you found out about some horrible thing she does that's a terrible deal breaker) all the better for you! Now you can refocus your energies on finding someone that will work!
Man I don't know why my attempts at relationship advice always turn into these giant ramble-fests, but I guess what I'm trying to say is that asking girls out is hard because you're thinking of it as a big scary hurdle that you have to clear before you can get that thing you want (someone to do stuff with you and occasionally have sexytimes) rather than test #1 for you to see if you are compatible with this person. The main takeaway from any of this you should be making is to interact with the person, listen to what they say, get a feel for who they are, and ask yourself at every step of the way "would we work as a couple?". The worst thing you could do would you to listen to her and then try to mold and contort yourself mentally to try to fit the right shape you think the girl would want you to be (that is - don't tell yourself "Yeah I could be a vegetarian" when you were just telling your roommate that you would LITERALLY die without bacon). The important distinction to not here is that I'm talking about you on a personal level. I'm not talking about lying to her to get into her pants - obviously don't do that - no, I'm talking about not lying to yourself so you won't have to stop pursuing her. Convincing yourself you can make something work when it's obviously not going to work. Another example of doing this is convincing yourself that this one is perfect for you because she'll fix some perceived fault of yours. Like pursuing some social butterfly because you think you're too introverted and she'll get you out there talking to people. That's bs. It won't work. That's what people mean by "be yourself". Be honest with yourself.
The question you should always be asking is "will she work for me?" and not "will I work for her?" Whether or not you work for her is for her to decide. So let her worry about that. You do you.
