Hi, I have been dating this guy for a year and a half. It was my birthday recently, and he gave me a ballpoint pen (silver handmade expensive) but I didn’t want something like that at all. He doesn’t seem to know me. And a few days after my birthday is his best friend’s, who asked him to be a groomsman (not even best man, so you note.) But because friend is busy with work, he can’t really celebrate his birthday. My boyfriend commented during lunch how he wants to throw his friend a birthday party. I said, “wow, I wish you had done that for me.” This goes back to more than birthdays, of course. He says he is always, “bros before hoes.” In the past my boyfriend told me that his friend could always make him feel better when I sometimes make him feel worse when he too down for unknown reasons. I feel like I give him more sobering perspective as opposed to, “it’s OK. Let’s drink beer.”

My boyfriend complains about stuff such as “what if years from now, I have a job that I hate?” And I have to listen to this as if no one in the world hates their current state of employment! He also takes his friends out (about 4 times) for wine tasting, but I had to ask him for months before he did that once with me. I think I am supportive because I do listen to him complain about everything that stems from his insecurities. He leaves me with comments like, “you make me so happy,” “I don’t know what I will do if you leave,” and “I love you more than anything.” I also try to help out financially when he complains about being poor. But I never feel like things are connecting.

We are both students and live about 5 hours apart from each other. Whenever I visit him, we have lunch with his friends at least once. I also had to hear about him go on and on about how he will miss his friends once they graduate and leave. One time, I was trying to tell him something serious about my parents but he was upset that I wasn’t focusing on how his friend will move away in 3 months. The good part about the relationship might be that we get along pretty well and he does seem to love me at least emotionally. But the sex has not been earth shattering, his self esteem is bringing me down too, and he is more excited and thoughtful towards his friends. My boyfriend is 25, and I am a few years older than him. It may take some time but how long should I wait?


Dear Shelley,

Ready for Lasting Love?
Ready for Lasting Love?

Before I answer your question, I’m hoping you could answer mine.

So, I’m working at this marketing company for the past year and a half.

To answer your question, answer mine.

When I started there, I thought it was a dream job. Yes, I had to commute. Yes, the pay was low. But I really thought there was potential for growth there. Now I’m having some second thoughts.

First of all, I work my ass off for these people and I rarely get any positive feedback. And if I’m not getting a better salary, the least I could get is the pleasure of knowing I’m doing my job well.

Second of all, I’m not that crazy about the way I’m treated by my boss. He’s kind of moody, and I get the sense that he prefers my co-workers’ company to mine. Maybe it’s because he’s known them longer, but he’ll make lunch plans and weekend plans and rarely thinks to include me.

Third, the job isn’t as fun as I thought it would be. I’ve heard that in life you should hope for an 80/20 rule — 80% of the time you’re enjoying yourself; 20% is “work,” but this feels like the opposite. Most of it is drudgery — paperwork, meetings, passing things through the hierarchy of the organization. It’s just not what I thought I was signing up for.

Finally, the company is kind of poorly managed. There’s a lot of drama and office politics that prevent it from running smoothly.  I know that I’m doing a decent job here — my boss has told me as much — but I just can’t help but feel that I don’t have a strong future at this company. One of my colleagues will get a raise or a promotion before I do, so I don’t feel that secure, fulfilled or happy at this company. What should I do?

When you read this email, the answer is quite obvious, isn’t it?


At which point do you take responsibility for staying in an unsatisfying relationship?

From here, the only thing that’s keeping you with your boyfriend is your sunk costs — the year and a half you’ve already invested with him. But would you rather invest another six months in a depressed, unemployed, shaky-self-esteem, 25-year-old frat boy who actually says “Bros versus Hoes” to his own girlfriend? Or would you rather cut him loose to find – I don’t know – a guy in his thirties who is happy, treats you well, and makes you feel like a top priority in his life?

Any reader of this blog knows that I don’t defend men who treat women inadequately.

By the same token, at which point do you take responsibility for staying in an unsatisfying relationship?

I say it should be now.

The fictional employee above should not ask for a raise, try to work harder, or make nice-nice with his boss. He should find a new company that surrounds him with high-caliber team members, provides stimulating work for good pay, and offers the potential opportunity for growth. If he stays at his dissatisfying company for 30 years, it’s nobody’s fault but his.

The good news is that you’re young. You’ll bounce back fast. And I think you’ll be quite surprised at just how easy it is to replace this indifferent slacker of yours. Good luck.