Bad timing or just bad?

As I mentioned yesterday, the next Love Letters event is Feb. 22 at Naga in Central Square. It's a party we'll co-host with RadioBDC, and it'll feature a performance by Benjamin Francis Leftwich, a very wonderful English singer-songwriter.

The show is free -- you just have to register at Please put "LOVE" in the promotional code area when you sign up. That will put you on my list. (If you signed up yesterday without the code, feel free to re-register to get on the Love Letters list so I can make sure you get in.)
Also, to those who have self-help books: Your homework is due.

Dear Meredith,

I recently moved to Boston to start a new job. I finally feel like my life is beginning and the sky is the limit but, when it comes to my relationships, not so much.

In September I started a casual relationship with a fellow alumni after meeting at our alma mater's football game. We instantly hit it off with similar interests, activities, and sense of humor, which is huge for me. Over the course of about 2+ months, things were going in the right direction, and I basically assumed we were seeing each other. Talking every day, making plans, etc. Although things seemed great and in forward motion, there were two big clouds that seemed to hang over it all: his long-term ex-girlfriend, who broke up with him only a couple months prior (she happens to live in my apartment building; I had no idea), and my ex-boyfriend who just so happens to be his friend. I hadn't dated this guy in years, and now suddenly they had started hanging out ... just my luck.
Things took a turn for the worse in November, and he put an end to it all, claiming he was not over his ex, he didn't want to hurt my ex (his friend), and that we just were not on the same page. I was heartbroken and thought I'd never hear from him again. Well, a couple weeks later I did, and it fell right back into old times, then he would disappear. A couple of weeks would go by and then he'd magically reappear. It is a cycle that I can't break because I care about him, and a part of me is afraid of losing him and still believes that we should date.

This seems completely naive, I know. I do not fall hard often, and usually think more like a male when it comes to relationships; I freak out and get bored easily. Maybe it's wanting what I can't have? I don't think so and I'm pretty sure I like this guy a lot and can't get over the fact he's either not ready, or just doesn't like me back -- which is a hard pill to swallow considering I thought he was overzealous in the beginning and wasn't even sure I wanted to date him.

I'm scared to tell him this cycle needs to end for fear of not having him at all, but I know I can't keep doing this. It leaves me feeling used and empty. All the dirty martinis in the world can't shake this. Thoughts?

– Against the Odds

"I'm scared to tell him this cycle needs to end for fear of not having him at all, but I know I can't keep doing this."

You know what you have to do, ATO. This cycle is terrible, and every time you sit around and wait for this guy, you're missing out on expanding your community in Boston.

You started this relationship because you wanted to meet someone nice. You're willing to put up with the exes and the risks. If he isn't and only wants to hang out in secret when it's convenient for him, there's nothing in it for you. Let him know.

I understand that you're scared of losing him, but he's not yours to lose. Do your future self a favor and spend some more time adding to your inner circle.

And speaking of inner circle, I must say that this alumni group sounds like it might be an extension of college. Exes in the same building, passive-aggressive hookups, and poor communication. You shouldn't have to deal with any of that stuff. (Except for maybe the ex in the building. Welcome to Boston. It's a small world.)

Readers? Is this just bad timing? Will he come around? Does she have to cut it off? Why is she so into this? Help.

– Meredith