I’m a college sophomore – and I have yet to have my first kiss. It’s not that I’ve never had guys show interest, they just never seem to be the guy I am interested in. Not to toot my own horn, but I think I am a reasonably attractive, funny, smart person, and I have seen way less attractive, stranger people have relationships or frequently talk about the people they hooked-up with over the weekend.

I’ve never been one to take initiative on asking someone out – I have an extreme fear of rejection. I also tend to be self-conscious about chatting up guys at parties. I’m always worried about wasting their time, or if they really want to be talking to me so I end up being sort of awkward. I also tend to crush on guys that I think are out of my league. My lack of experience is getting to an embarrassing point, and I don’t know what to do! Help me, Tuffy Luv, you are my only hope.

Hopelessly Hoping for…Anything

Dear Hoping,

Girl, I’m flattered (and intrigued by your Star Wars reference). But you don’t need me–you already got you! Now let’s go through your letter piece by piece, and lil’ ol’ Tuffy’ll tel you what you can do:

(1) Okay, you say the guys who show interest in you are never the guys you’re interested in. First red flag. Hey, this is a great sign–it means there ARE men interested in you, which is a good sign! But it’s like Groucho Marx said: “I refuse to join any club that would have me as a member.” In other words, it’s like, if they think you’re good enough, you assume there must be something seriously wrong with them. Bad call, girl!! They like you for you–that makes them SMART, not damaged goods!

(2) You talk about your good qualities. Great! You should know that you’re cool and you should be able to talk about your good points! But then you put down other people in the next sentence, saying that you “have seen way less attractive, stranger people have relationships.” Tsk, tsk, honey. Don’t put other people down to make yourself feel better. It ain’t never gonna work.

(3) This “extreme fear of rejection–” okay, NOW we’re getting at the problem! This is the REAL issue, Hoping. This is what everything else in your letter is basically getting at. THIS is the actual problem, and THIS is what you have to work on.

My prescription, girl, is that you go to more social events and you make it a goal each party to have a real conversation with one guy. Just one guy. Eventually, it’ll get easier, and you’ll start to see that, if they’re talking to you, it’s because they WANT to talk to you. Otherwise, I mean, otherwise they’d just walk away! And some might, but that’s OK! Just move on to the next person. There will be plenty of guys out there who will stand there, chat it up with you and even put their arm on the small of your back (then pull you in for a smooch).

So get out there and get brave. And I guarantee you’ll get your kiss. More importantly, you’ll gain confidence, and that’s what it takes to form a relationship. First kiss, first shmiss.

Hearts & Skulls,
Tuffy Luv