Crushes on Professors and “How Can I Tell If I’m Boring?”

by A Lady

1. I’m going to keep this brief. Basically, like many before me, I have a crush on one of my college professors. I wouldn’t consider anything other than a little flirting until after I’m done with his class, but do you have any tips for seducing him? Maybe some subtle-but-effective flirting techniques? Also, without really knowing much about the situation, what are my chances?

I have no tips and if your professor is a stand-up guy, you have no chances.

I know, I know, I’m very cruel! There are happy couples ‘round the world who met while one was teaching the other, and for good reason — it’s intoxicating, sitting below a handsome (I’m assuming), older (I’m guessing) man and feeling the weight of his perceived wisdom envelop you.

For every happy ending, though, there are five messes. Probably more.

Working really hard and getting an A from this professor will feel infinitely better than having his eyes linger too long over your decolletage, if he’s into that sort of thing. If he’s not, a flirtatious student could make things difficult for him — most professorial contracts strongly frown upon fraternization with students, and a even the rumor of indiscretion can stick for years, or longer.

The silver lining, though, is that these kinds of crushes can be good opportunities to think about what qualities you might value in a romantic partner — is he funny? Kind? Confident? Pick out the things you like most about him, and keep them in your back pocket when engaging with possible paramours who aren’t directly affecting your GPA.

2. How can I tell if I’m boring, and what am I supposed to do about it? I’ve been working really hard on liking myself, and I’ve come to a point where I could name several things that I appreciate about myself, which is a lot better than I was doing a year ago. But I can’t shake the suspicion that I’m just boring. I mean, I think I do some pretty interesting stuff: I work two jobs, write for and edit a well-respected niche magazine, plan some fairly successful events, and generally go out around six nights a week. I’m pretty well-educated and well-read, I try to keep up with current events, and I have strong opinions and (I think) a good sense of humor.

Still, I am pretty convinced that I, as a person, not what I do, am boring. I’d say that about 75% of the times I consider expressing an opinion, telling a story, or making a joke in a social setting, I realize “This is boring and no one will care!” and keep it to myself instead. I’m good at small talk, listening, and any sort of conversation in which I have a goal (see: event planning). I just feel like I can’t contribute anything most of the time. I don’t need everyone in the world to find me fascinating, I would just like to feel that there is some subset of people who think I am interesting, preferably a subset including myself. Help?

A year ago I moved from one city to another. Nervous about my prospects, I mentioned to a friend that I felt anxious about seeming interesting and likable. “I’m too normal,” I said. “I won’t seem exciting enough.” My friend laughed and said I was, in fact, preternaturally down-to-earth and that that would make me shine. I say this not to boast about my own sparkle, but to remind you gently that everyone feels nervous about being well-received, and also that the only truly uninteresting people are the ones who talk of nothing but how interesting they are.

May I ask, O Interesting Person (I, for one, am interested in how you find time to work two jobs, write, and go out six nights a week, and I’d be willing to bet money on the fact that many of the people you see socially are also fascinated by your energy and how thoughtful you are in spite of all the things you have going on), how much time you spend hanging out with just yourself? It sounds like you’re spread awfully thin, and while I’m not judging your choice to do as much in a week as I do in a month, I wonder if all this activity keeps you so engaged with the world outside your head that you don’t get much of a chance to appreciate how fascinating you really are.

3. I met this girl through a friend of a friend and we exchanged numbers and started talking a little. We eventually went on a date, and she told me that she wasn’t really ready for a relationship, just looking for someone to hang out with. It let me down a little, but since I’m new to the area it was nice to meet a friend. Anyway, we go out to dinner a few times/meet up for happy hour, just kind of shoot the shit. Sometimes she’d seem really into me, other times not so much. After one night at a bar, I walked her to her car and went in for the awkward hug. I didn’t want to push the whole “LET’S MAKE OUT CUZ WE’VE BEEN DRINKING” card since she said that wasn’t what she was looking for, but I could immediately tell she wasn’t looking for a hug. As I sulked back to the bar, I couldn’t really figure this out. Was she being serious about the whole “no relationship yet” thing, or was she just trying to play it cool? Should I have kissed her? A Lady, you’re my only hope.

(If it helps, I’m 24 and she is 28.)

My first thought was to ask you if, when she said she was looking for someone to “hang out with,” she meant “hang out at the bar and watch the game” or “hang out in bed,” but upon further reflection, I don’t know that it matters.

You did the right thing in not kissing her — if nothing else, it says you’re the kind of person who takes others at their word, which is an admirable quality. What’s up with this girl, though? Twenty-eight is old enough to know that telling someone you don’t want to date them and then angling for a drunken parking-lot kiss isn’t particularly mature or respectful or nice. If she’s genuinely changed her mind and wants to try dating you, it’s on her to come out and say that and not play coy and seek your romantic affection when it’s convenient for her.

Do you even want to be friends with a person like that?

4. I lost my virginity to my boyfriend of over three and a half years, and I’m craving having sex with someone else. BADLY, as in if I’m hanging out with another guy I start throbbing and I almost want to cry from holding back. The thing is, I will probably never break up with my guy to feed this terrible, terrible craving, because he was diagnosed with cancer a year ago, and we have both been emotionally/physically shattered from it. He is cancer-free now, which is amazing, but we are both depressed, anxiety-ridden, and are constantly bickering, because that awful experience cannot stop replaying in our heads.

Here’s where my stupid brain and loins make matters worse: I have a couple of best dude friends that I can’t stop thinking about sleeping with. Back in high school, we’d essentially done everything but the deed, so there is indeed history with these gentlemen, and it’s driving me mad being alone with them because I remember what it was like to hook up with them years ago. I’m scared because I do love my boyfriend, or else I wouldn’t even still be with him, but I almost just want to drag my dudes into bed to get this feeling over with. Yet, I’m also worried of giving in, sleeping with them, and then never having the same relationship with my b/f AND my friends ever again. Or, it could go perfectly well. I don’t know. I would just bring up these weird cravings with my b/f, but I am very confident he would turn, aggressive because he’s had waves of that throughout this whole getting-over-illness period. I don’t want to stress him out any more than he is now.

I’m writing for advice because I would never confide any of this to my family or friends, and I need an outsider’s view on my situation. What would you do if you were me?

As a regular reader of advice columns, I sometimes feel like it’s a cop-out when a columnist advises someone to see a counselor, because yeah, we should all be in therapy anyway!

AND YET, dear reader, this question is out of my depth. You and your boyfriend have issues you need to work out on your own and (should you choose to stay together) together, and I think those issues would be best worked out under the guidance of a professional — ideally I’d suggest couples counseling, but it would probably also be useful for you to see someone on your own, especially since you say you would never feel comfortable talking to anyone in your life about this. Sex, depression, anger, cancer! It’s too much for one person to navigate alone, Person!

I will say this, though. Do not drag your friends into this mess by trying to have sex with them while you have a boyfriend, no matter how much you may want them. That’s unfair and you know it.

5. The other day I was having sex with my boyfriend when he texted someone. While he was still inside me. Idk who it was I just heard the clickclickclick on his iPhone. What exactly does this mean? Was he just not that into it or was he just putting on a tough guy act to seem cool. Please help!

Does your boyfriend have a parent in the ICU? No? He has no manners and you should dump him immediately, preferably by text message.

Previously: Sensual Shampoos and “A Mutual Love of M*A*S*H.”

A Lady is one of several rotating ladies. Do you have any questions for A Lady?

Photo by Elzbieta Sekowska, via Shutterstock