Reader question #71: Should I patch things up with an old friend who hasn’t always treated me very well?

Dear Captain Awkward,

I never thought I’d write one of those weepy “Should I cut things off with my friend?” letters to an advice column, but here I am. Long story short, I’ve been taking an extended (18-month) time-out from my best friend and now he wants to get back together. The problem is that I’m not myself due to a traumatic bereavement four months ago. I’m getting help for the resulting depression and insomnia, but I don’t feel like I have people to confide in about this particular issue, and I don’t trust my judgment in this state. I know that that my former BFF and I can’t go back to the way things were, but I’m tempted to at least patch things up and see what can be salvaged. How can I figure out if I should continue to keep him out of my life or try to find some new relationship?

“Bill” was my housemate in our senior year of college. We didn’t really get along at the time because I was the nerd and he was the one with a steady stream of live-in girlfriends and no clue about what he was doing next. He and our other housemate drove each other insane and I stayed out of it. There were a few bonding moments, but after school we didn’t hear from each other for 5 years.

I don’t remember exactly how Bill and I started talking again, but we saw quickly that we each had something that we could help the other with. I’m a writer and good at resumes, interviews, and job applications, so I coached him on getting an assistantship to pay for his grad school, and a good job on the side. He’s good with women, so he helped me move from “beyond hopeless with women” to “not entirely hopeless.” There was always this transactional part to our relationship, but we built up a real friendship, too. We lived far apart and saw each other in person twice a year at most, but we’d talk on the phone nearly every morning and evening. He was my best friend and he told me that I was his. He asked me to be his best man.

This went on for three years. I was a kind of communications director for him, and he was my date doctor. Things started to go sour when he read “The Game” and put together a persona as a date doctor for hire. Guess who got talked into spending a huge amount of time editing that alter ego’s web site, writing down the things that I’d learned, and listening to Bill crow endlessly about how good he was with women? On the other hand, the recession had hit and before I knew it I was doing job-search consulting for Bill’s fianceé, brother, sister, dad, and a friend or two. My dating help fell out of the picture, except for a young lady that I met on my own, who ran for the hills after she saw pictures of me with a sleazy pickup artist on facebook. (Thank heaven for the “That’s not me in this picture” button.)

Around this time Bill got a lead for his dream job in one of those sunny cities on the coast. That job became an obsession. It was all we talked about. We went through a dozen drafts of every email and document that he sent to the company, and we rehearsed every phone conversation and interview that he had with them. Sometimes this went on for hours, until I was too tired and frustrated to go on. He’d say “I understand how you feel, but I can’t think about anything else.” When I answered the phone, he would immediately launch into questions or news about the job. I told him that his phone manners had become a problem; I asked for the courtesy of a “Hey man, how’s your day been?” before getting to business, but he couldn’t restrain himself to do that. I knew I’d had enough when he called on my 30th birthday and again went immediately into the news about the job. I said “now’s not a good time” and kept trying to stop him, but he said “can’t think about anything else — here’s what I need from you today.”

That job application process had started in February; he got the job in December. When he told me, I said “Finally!” and hung up the phone. I had intended to take a break, but found that I didn’t want to call him back or answer his calls. He got the message after a month or so and stopped calling. We had no contact for a year and a half.

In the meantime, I dealt with a stressful loss of a family member that has left me with something akin to PTSD. I’m getting help, including a therapist and meds, but this is one of those things that will take time to get over. About two months after that event, Bill sent me a public “let’s catch up” tweet, and I wrote back privately to say that my [close family member] had died of a [type of medical clusterfuck], that it had affected me seriously, and that now was not the time to catch up. I thought a “sorry for your loss” response would have been polite, but instead he tweeted a picture of us from the good old days with no explanation. Coincidentally, the date doctor alter ego has reannounced himself after a few years of silence and also tweeted about me once by name. I think Bill wants to get back together or at least talk. Maybe he’s finally going to make an honest woman out of his fianceé and still wants me at the wedding, or wants to tell me that I’m no longer invited.

He’s coming across as a jackass because you’re hearing my side of the story, in my stressed-out, sleep-deprived, bereaved condition. Before you say “don’t ever talk to this jerk again,” know that Bill and I had good times and that we trusted each other. That kind of a friend would be really good to have right now — I’ve been surprised at how few people are willing to talk to me about the medical clusterfuck. I know that Bill and I can’t go back to the way things were, but sometimes I feel like we might be able to talk at some level again; other times I remember how manipulative and selfish he can become when I need help. I’ve wondered if this is what it’s like to be a battered woman who can’t leave the guy. How can I get some clarity and make a good decision?

Thanks,
Trying To Figure Out How This “Friend” Thing Works

Yours is a hard letter to read, because “Bill” does come across as a total user who tapped you for a lot of free career coaching and resume writing and web copywriting, and even managed to turn the stuff where he supposedly helped you in return into a plug for his own “business” ventures. I suspect that even if you were less stressed and sleep-deprived and could include all possible sides of the story, I would still be giving “Bill” the big old side-eye.

You did the right thing by cutting of contact and giving yourself some breathing room.

I’m really sorry for your loss and the trouble you’re going through right now.

Okay. I probably officially hate “Bill,” and I think your life is probably way, way, way better without him. But if talking to the guy who knows you from way back will give you some comfort during this really difficult time, then you don’t have to cut him off just to make me happy and sustain my belief in justice and karma. We all maintain imperfect relationships with imperfect people for our own good reasons, and you don’t have to justify yourself to me.

So, this becomes a question about reciprocity, boundaries, training yourself to manage your expectations around certain people, and re-training them about how they are allowed to act around you. If you do end up reconnecting with Bill, how do you manage the relationship so that it’s more of what you need and less of a timesuck and soulsuck?

Friendship is based on equal parts affection and reciprocity. Yes, friends help each other write resumes and gain confidence with chicks or hang curtains, but we also just, I don’t know, invite each other to hang out and ask each other how we’re doing and stuff, simply for the pleasure of the other person’s company and not because we plan to get anything out of it. “Bill” does not appear to understand this.

Being able to set boundaries means that you can say “Hey, I don’t have time/don’t feel like solving your career problems today, Bill, I’ve got some shit going on and would like my friends to ask me how I’m doing instead of asking me for help” and having a reasonable expectation that Bill will say “Man, I’m sorry, I was acting like a jackass right there. How are you? What do you need from me?” In other words, it means that you can stand up for your needs within your relationships, and still feel okay and like you are deserving of love and friendship. People with poor boundaries let their friends walk all over them because they are afraid that if they ever say “no” their friend will hate them or leave them. Allow me to invoke Captain Obvious for a second: That is unhealthy. You’re in therapy? Good. Your therapist can help you with this.

Managing expectations about your relationships means accepting that some people are just not going to give you what you want or need. You completely deserve “Bill”‘s gratitude, attention, apology, and respect, but that doesn’t mean you are ever going to get it, and if you go into interactions with him needing that stuff, you’re going to end up hurt and frustrated when you don’t get it.

So, this is my advice for dealing with “Bill” in the future in a way that protects yourself:

1. Keep your interactions light and short. Make him a “small doses” friend.
2. Say no to all requests for favors. “Sorry, can’t help you, dude. How is your fiancee doing?” Don’t explain why you can’t, just say that you can’t and change the subject.
3. If he starts to piss you off or hurt your feelings, get off the phone. “Good catching up with you, I need to go take care of some things. Bye!”

I don’t think that “Bill” used your time apart to reflect on what he did wrong and attend Friendship Academy, and I don’t think he will magically become a giving, concerned, helpful friend, but I think he will respect boundaries if you consistently set them and let him know that you are not Endless Favor Guy anymore, and maybe you can figure out some stuff that you still have in common. If not, it’s okay – you can always carpet bomb his house with African Violets down the road.