originally published September 12, 2007

I'm a graduate student in a committed, happy relationship. My girlfriend and I live together and she is great: positive, beautiful, smart and a lot of fun. The problem isn't necessarily with our relationship, you see. She dropped out of college a while ago and is working at a typical part-time job. Lately, she has been growing more and more unhappy, feeling like she doesn't know what to do with her life. She feels worthless, unmotivated and like a "nobody." She is considering getting back into school, but doesn't see the point because she has no idea what she wants to do with a degree if she were to get one. Basically, she feels like she's wasted all of her potential. I hate to see her feeling like this and I also feel completely powerless.

I'm also confused about how and/ or why I attract this type of woman. I've been in three relationships that lasted over a year, and each of these women have felt similarly lost, confused, unambitious and unmotivated. Each time, their unhappiness associated with this got them so down that they became unable to continue to invest in our relationship, and it wound up breaking us apart. I desperately don't want this to happen in my current relationship. I'm looking for a little advice and also some answers as to why I seem to be a magnet for this type of woman. I don't think it's that I seek them out; in fact, I'm attracted to driven, career-oriented women in general. Is there something I'm doing to cause or exacerbate this? Jyl, I could use some wisdom.

Concerned Boyfriend

Tell your lady I said, “Welcome to the Club!”

I would caution you against assuming that just because somebody works a crappy job that they are unambitious. In my experience, having too much ambition can be just as paralyzing as not having enough. Having a wide variety of interests makes it difficult to decide which one to pursue. You should encourage her to try to figure out what she is most interested in and best at. There are tests you can take (I’ll bet you can find them online) that tell you what type of work you are best suited for based on your answers to a simple questionnaire. Also, taking a class in something, volunteering or finding an internship is a good way to see if you might be suited for a career without investing a lot of time and money.

Why you attract this “type of woman” is likely your age. It used to be that a girl graduated from high school, got married and had kids. Happy (or “Happy”) housewife. End of story. Then women started going to college. Some of them had a career and kids, but some still chose to be stay-at-home moms. Now that women can do basically anything from stripping to fighting fires to waiting tables or working in a lab, there is quite a bit more room for existential angst. The general feeling of rudderlessness tends to happen in the twenties and early thirties, and I would guess that this is why you have repeatedly dated women in this situation. Also, you live in a college town, and lots of people get into college and discover that either a) they can’t hack it; or b) they don’t want to, because they have no idea what they want to do and they realize that getting a random degree is a gigantic waste of time and money.

I'm a gay girl who is falling for a straight girl. Now, before you tell me to turn the other cheek, here is why I need your help: this "straight" girl doesn't act so straight when she and I are alone together. She constantly tells me that there isn't a chance for her to become gay or have a one-time lesbian experience, yet when we are alone, she strays away from her claim! We share a lot of the same friends, and with her acting the way that she does, they get the impression that I am some lovesick lesbo going after the wrong person. What they don't see is that she constantly flirts with me and she treats me how she would treat her boyfriend (if she even had one). A few friends have already caught onto the sexual tension that exists between the two of us, but they think it is because this girl is just lapping up all the attention and flattery she gets from me. We spend a lot of time together and she has even told me that if I weren't a girl, I'd be the perfect kind of guy for her. A part of me feels like if I am just patient, maybe that moment will eventually happen between us or maybe I am so fixated on a fantasy that I can't see how cruel she is actually being to me. At the same time, we spend a lot of time together and we actually do have a great time when we are in each other's company. She tells me there is no point in hitting on her or flirting with her because she isn't going to "budge," but then she constantly initiates flirting with me! What should I do and what do I need to say to this girl?

Anonymous

I don’t know what your definition of “flirting” is Anon, but the girl has made it very clear (at least verbally) that she is not going to date you, or even sleep with you, so you have to get over it. I’m not saying that she isn’t playing games with you, because I don’t know that. You haven’t given me enough information to decide that either way. I’m just saying that you shouldn’t participate. I suspect from her remarks (You’d be “the perfect kind of guy” for her? Please!) that she is enjoying the attention, and in a perfect world you would simply walk away from this situation before it gets any worse. I would say the same thing if you were a lovesick straight boy (or girl). But knowing human nature the way I do, I can only suggest that you shift your focus to a more attainable girl, and try to at least pretend that you are moving on. Maybe your “friend” will stop acting the way she does with you if she stops achieving the desired effect.

Jyl Inov

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