“Dear Dee,

I’m having girl problems. I like this girl a lot but don’t know how to ask her out. What do I do?

Desperate Dave”

[To ask “Dee” a question, email mdegen@jesuitcp.org, and we’ll pass it along.]

Dear Desperate Dave,

“The heart wants what the heart wants” I believe is the age-old adage to which your situation applies. Longings for love can yield either feelings of transcendental ecstasy or backbreaking emotional pain, with the latter, as sad as it may sound, being infamously more common.

With that said, my first and most important piece of advice is LOOK AWAY AND NEVER LOOK BACK. Don’t set yourself up for emotional turmoil. However, maybe I’m being a little too pessimistic.

So, I’ll attempt to give you what advice I can if you so choose to pursue what you think is so beautiful but will likely end up as so perturbing; if you choose to pursue that which is so pointless: a high school relationship.

What you must keep in mind is that high school relationships are not mature relationships, and cannot be fostered by such characteristics. Caring, kindness, affection, attention, being a good listener, being someone who is open to be talked to about anything, maturity, all of these “sweet” things that females apparently long to find in a male do not apply.

They can later though, so if this works out, you better be ready that guy and be him well. However, none of them really matter, from my observation. You have to be and act comfortably, be charming, and be aloof. You have to lure them in (not in a creepy way, you should know what I’m getting at). You cannot be the instigator of anything. You have to set up the instigation by the girl. You have to put the opportunity out there, but she has to be the one who jumps on it.

Don’t be too attached, yet don’t be too distant. Don’t be desperate (as your pseudonym implies), yet show attention. Don’t be overbearing, yet show that you care. It’s a hard balance to achieve, but, when in doubt, act upon the option that is more aloof. You have to give her the opportunity though: go and talk to her, and gauge her response. If she seems interested, keep it going, and eventually develop it a little further: ask her to hang out indirectly, say: “let’s hang out sometime” or something of that nature. Once again, gauge the response.

If you get her phone number, initiate a conversation (usually by text in this day in age) and see how engaged she becomes in the conversation. Don’t overwhelm her; it is often a good idea to wait for her to engage you in conversation. In summary, high school relationships are meaningless and often just lead to negativity.

I stand by my cynicism.

However, having strong feelings for somebody of a romantic nature is completely normal, and are feelings that most want to act on, and if it works it out, it’s certainly freakin’ awesome, so I understand. Therefore, instigate conversation. Put the opportunity out there.

Be yourself and be relaxed, and remain slightly aloof. Let her come to you. If it doesn’t work though, it doesn’t work. Be prepared to move on. How’s that for the stereotypical and simplistic “be nice and be yourself and talk to her” relationship advice? I just took that nonsense to a level my friend. You didn’t expect this.

-Dee

P.S. Dave, don’t be desperate, because that’s sad. Don’t be like that, son.