A Conundrum

I'm so sick of being poor.

An ex-boyfriend of mine (on and off again for nearly 6 years) recently offered me a job working for his web 2.0 firm making $20,000 more than I make now. Should I give up my (2 years worth of) social work career, the two years of school and $60,000 of debt (which I can barely repay on what I make now), and the two years of hard work at my public hospital job?

It's a tough call.

First of all, it is an ex-boyfriend who, of course, I am not yet quite over, even though he's now had a serious girlfriend for about a year. I also happen to be pretty close to his family, his younger brother and sister, his mother--I was even at the hospital with all of them when his father died of leukemia, about a year ago.

This "boyfriend" and I really only dated, officially, for about four months. We broke up sort of because, early in our relationship, his brother kind of hit on me, and I, being an impulsive 23 year old with no long lasting relationships to speak of and curiosity, drunkenly tried to kiss him. After this, instead of being a tough girl with a lot of confidence, I sort of groveled to maintain a relationship with him (I highly don't recommend to anyone with any semblance of self-respect, but I was young, insecure, and pretty much alone in NYC) and so we continued to spend a lot of time together, watching movies, having dinner, going to see bands, and yes, having sex. In retrospect, I was probably more like a geisha than a prospect--He's Lebanese, i'm Jew-ish, he's religious, I'm not, and despite knowing more about indie bands than Pitchfork.com and being pro-Israel, he's a pretty traditional Arabic man, and well, I'm a bit of a feminist, even if i dont always admit to it. It's likely he never really viewed me as a potential mate. Probably more like a fun girl to hang out with in the interim. Sure, he and I occasionally discussed the long term, but he always gave me evasive answers like, "Well, I cannot commit to anyone right now because, I still have so many other responsibilities" (mostly meaning taking care of his dysfunctional mom and dad)" or "I love you but we want different things and ultimately it wont work." Sometimes he commented on my impulsivity or lack of maturity which is funny, because he is now dating someone 11 years younger than him...but I am not bitter. Much.

But I have to admit I haven't been all victim in this relationship. I've reaped a lot of benefits from knowing him and his family. I've gone to see a lot of bands I would otherwise never have heard of, I've been able to experience having brothers--well, okay, I have one--but I meant in a good way. I've eaten in a lot of fancy restaurants I could never afford, I've gone on fun road trips, and I've had great conversations about music, film, and politics. Even more so, he's comforted me during times of sadness and confusion, and I've been able to share many holidays in the warmth and comfort of his family's home.

I began to be a bit more comfortable with the idea of us not being together about two years ago, when I had a serious boyfriend and now he has a serious girlfriend. Although I used to wish to grow old with this man and envisioned sitting on benches in Italy or Brighton Beach with him at the age of 82, I've recently been able to come up with numerous reasons why I really shouldn't want to be with him anyway...

So today there is an offer, an offer that's been thrown out a couple of times but not as seriously, to be a technical writer at his company...The job has many perks. It is in midtown Manhattan with a group of young, varied and interesting people, a few of whom I already know and am pretty good friends with. It would utilize some of the skills that I have developed: writing, interacting with people, and business and analytical skills, though it would not use, per se, my well-honed ability to empathize and help the underprivileged...

But man, right now I am living paycheck to paycheck. G-d forbid I have to fly to visit my father, g-d forbid my cat gets sick. When that happens, any negligable amount I've been able to save disappears. And that is a scary feeling. Especially for someone my age. And there is no rule that says I cannot go back to social work, or something like it, in a few years. Indeed, I would likely have the money and energy to take classes in the evening to provide the more clinical and/or psychoanalytic training that I would need to have a private practice.

And maybe more importantly, it would be a great lifestyle change--instead of being stuck in the depressing, isolated ghetto neighborhoods where social workers are wont to go, with no where to meet anyone for a drink, or lunch, or even coffee, I would have the vast playground of Manhattan at my disposal. I mean, sometimes, I get really upset that I pay New York rent and taxes to live an hour away, work in a miserable neighborhood, and get to maybe enjoy the city one day a week, at best. And I've made no friends at this job because everyone is older and/or settled into their lives and not looking to add anyone to their social roster (besides the social work director, who is 72 and brilliant and feisty and inspiring, but I don't really see us getting drinks any time soon). I'm too cute, single, and social to sit home on Saturday nights.

But how can I handle our history? Can I handle business as just business, or would my unresolved feelings get in the way?

Sigh. Not to mention, my dad has serious reservations about me working for him. For practical reasons, because it is a new company, he's worried that it is some fly by night start-up with no benefits that might collapse tomorrow. He's old school, he worked at his city job for 30 years and then retired with a pension. He also knows some of our contentious history and, as a father, does not exactly trust a man who from what he's gleaned, treated his daughter like a mistress from time to time.

Well, it's something to think about, I've got plenty of time. I mean, it's not like I can afford to go out any time soon.

Especially now that my potential future boss isn't trying to get in my pants.