Hi Captain,

I (she/her) am 39 years old and haven’t had a real friend since I was 23. Due to numerous instances of abandonment and rejection before and since, I’ve developed a form of Social Anxiety where I panic whenever I think someone important to me might, well, abandon or reject me. I’m working on this with a lot of self-help and meditation, but I need some help with my current situation.

Two years ago, I met a guy my age at work, who is very successful, a young executive at our very large, you’ve definitely heard of it company. Upon discovering that we have a lot in common, and I was struggling with a miserable job situation at the time, he quickly became my mentor, and from there, we’ve become friends.

Here’s where it gets weird. Despite the fact that we talk about deep, personal, obviously non-work related subjects, including things like God, anxiety, self-doubt, spiraling down into dangerous depression, etc., he has refused to meet me outside of work. These deep meaningful conversations occur in 30 minute scheduled meetings once a month in his office. He won’t even give me his personal cell phone number, using his work mobile instead. (P.S. it’s not because I’m a married woman and he’s a married man. We had that conversation. Also, most of my invitations have been for us to do things with our spouses in tow, and my hubby is fully supportive.)

Background on him, he was formerly a soldier in Iraq, and his best friend was killed there. It messed him up pretty bad, and he did go to therapy. He has stated he has no friends (and supposedly he likes it that way). I suspect he erected these walls to protect himself from ever experiencing that kind of pain again. I think he is struggling because I’ve managed to get through his defenses, and he cares about me. He always genuinely appreciates me being a good friend- checking on him when he’s sick, sending him goofy memes to cheer him up when he’s stressed out (which has been a lot lately), etc. The verbal and written work/life barrier has been thoroughly crossed. He just won’t cross the physical work/life barrier.

Anyway, it’s been taking him longer and longer to say no when I invite him out, and it’s obvious to me that responding to my invitations causes him tremendous anxiety. It’s like he really wants to say yes but talks himself out of it. At our last meeting, after turning down my latest invitation (with a “probably not” following a full week of deliberation), he said that he was now willing to meet outside of work, but it has to be something really small, like lunch (which is impossible with his schedule). So far I haven’t found anything small enough, and he’s made no suggestions.

Because of my anxiety, every time he tells me no, I freak out and spend a day or two crying, unable to sleep, etc., until I’m able to get a handle on the negative thought train and shut it down. I’ve considered giving up on him numerous times, but I can’t do it because he gives excellent advice, I feel so comfortable talking to him, he understands my pain, he makes me feel good about myself, basically I need him to talk to, and I feel like he needs my help too. Everyone needs a friend, and I might be the only person persistent enough to keep trying with him, BECAUSE of my anxiety. And he’s SO CLOSE now. Admitting he would go out was huge. But I’m also frustrated and tired of the roller coaster ride of emotions (as is my husband.) To make matters worse, I turn 40 in two months and all I wanted was to be surrounded by friends, but I can’t even get one friend and his wife to go somewhere fun for an hour and have dinner after. I’m having a hard time staying positive. What should I do?

-Best Friend by Default

Dear Best Friend by Default,

I preserved your email subject line, for the most part. There is…a lot…going on here, and I am going to try to be as gentle and helpful as possible, and I am going to turn off comments (you…do not…want to read them, trust me), but I do not think you are going to necessarily like anything I am going to say.

For all of 2019 (at least), I want you to stop inviting your friend/mentor to do social things outside of work or doing anything to try to “get through” to him about this. If he wanted to give you his phone number, he would. If he wanted to hang out outside work, he would. If he wanted to make time for lunch in his schedule, he would. If he has traumas or anxieties that are getting in the way of being more social, those are his to work on. The idea of “getting through someone’s defenses” referring to a coworker who has told you he doesn’t want to hang out because he has PTSD and is grieving for a dead friend? NO. PLEASE STOP NOW.

Thirty pleasant minutes once a month in his office is what you get, unless he seeks you out to indicate otherwise. He knows you’d like to get drinks or lunch sometime, he doesn’t need reminding, and you need to stop. You say that it’s “obvious…that responding to my invitations cause him tremendous anxiety.” Knowingly causing a friend tremendous anxiety, to me, is a clear sign to stop doing the thing that stresses them out. “Exposure therapy,” where someone with an anxiety or phobia does the scary thing in small doses to gradually increase comfort, a) has very limited application and can often make things worse b) is done in collaboration with a clinician with the patient as the driver. We do not exposure therapy our friends or “break down their defenses” so they’ll have lunch with us on occasion. Say he were asking you to help him with this. Even then, your ethical path is to say “Friend, get a counselor, and then let me know when you want to try having lunch!”

Also, he’s your work mentor, so are you doing everything you want to be doing with your career? Is there professional mentoring he can give you that will help you with your career? When was the last time you updated your resume, or went after a promotion or a new project, or did some networking with others in the company?

It’s okay to make friends with coworkers, but I would advise you to redirect your interactions with this person away from cajoling him outside for a meal (a high anxiety activity for him) and back toward the original purpose that brought you together (work, probably much lower anxiety). In your shoes I would also make sure that electronic communications you send at work are about work. It doesn’t mean you can’t ever be friends, or talk about other things in your lives, just…listen…literally everything you describe about your interactions with this person is telling me that this relationship needs both breathing room and some structure. Like, I believe you that he really likes you and values your company? Because if he didn’t, this would have been an HR issue long ago. If it were me? Your ass was in HR roundabout the fourth time you asked me to lunch or for my phone number and I said no. When we mix work and friendship, we take on certain responsibilities to respect the environment and professional expectations. You are crossing some lines and you need to yank yourself back behind them.

You can address all of this directly with him if you want to, maybe try: “Friend, I realize that I’ve been pushing you pretty hard to hang out outside of work, and that’s so stressful for both of us. I’m so sorry, I’m going to stop doing that, let’s just focus on [work/mentoring/catching up at our monthly meetings] for a while, and if you ever want to grab lunch, you can let me know.”

But, honestly? You don’t have to talk about it, as long as you do it. And “This internet advice columnist said I’m overstepping, can you reassure me about that?” does NOT count as talking about it or fixing the situation. Even if he has poor boundaries, you can still readjust yours. If you can’t readjust your expectations and your approach to this working relationship, you need to reduce 30 minutes/month to zero minutes/ever.

Ok, that’s work stuff sorted. Now let’s talk about the rest.

It is not your friend’s fault that he’s your only one. He’s just a dude, he’s not your vision of yourself at 40, and he’s not the one putting you on “the roller-coaster.” You write:

“Because of my anxiety, every time he tells me no, I freak out and spend a day or two crying, unable to sleep, etc., until I’m able to get a handle on the negative thought train and shut it down”

This is not a normal or reasonable reaction to a coworker, even one you really like, turning down a lunch invitation. An outsized emotional reaction doesn’t mean you’re a bad person, you’re clearly suffering, so, let’s heed the warnings here, and find you some care and relief from that awful feeling.

I think you would benefit from some mental health support in addition to “self-help and meditation.” Like counseling, for starters. If your company has an Employee Assistance Program (EAP) you might start there with a referral, you might ask your primary care doctor for a referral. There are multiple online guides, and we have this old post to help you narrow down the right fit.

Letter Writer, I especially recommend therapy, specifically, as a path for you because a) you mentioned you have a great job at a fancy company, it’s more likely you have resources available to you, b) regularly talking to someone about all the stuff in your life and getting advice about it is already a thing you like and benefit from, c) a therapist is gonna have real clear boundaries for doing that, and, d) I would bet you $100 actual dollars your husband would choose never to hear your work dude friend’s name again if he could, he doesn’t think you’re trying to cheat on him but he is 99% like “whatever you want, dear” (please, let’s talk about something else), ergo, you need a different outlet. You need a safe place to channel all the feelings you are having, therapy/counseling of some sort is a good start.

With the advice and support of some sort of counselor in place, I also think you would benefit from actively seeking multiple outlets for socializing and meeting new people. I can’t promise you “friends by your 40th birthday” or “close friends to replace Work Duder!” or even “friends!” but I think there are many, many people of all ages who are seeking new connections. They feel awkward and nervous about it, they feel like there was something they missed that everybody else learned, or that they missed the window, they got divorced or moved across the country or left a toxic group or never had the knack and now they are trying again, to figure out how to meet new people and be in the world. You find them in churches, in improv classes, lessons of all kinds, dance classes, in hobby groups, sports and exercise groups, in MeetUps, in book clubs, volunteering, working on political campaigns, putting on amateur theater productions, and singing in choirs.

Cities have more variety than rural areas but people in rural areas need to leave their four walls on occasion, too, and I guarantee you that there is SOMETHING nearby where you live where you basically have to show up and be pleasant and other people will do their best to pleasantly tolerate your presence for a few hours and be mostly glad to see you when you come back. Pick something that interests you and try it out. Try to go back a few times before you make a decision about whether to quit or keep going. Keep your expectations low, if you treat everything with the goal of “make close new friends as efficiently as possible” you will set yourself up for failure, but if you reward and praise yourself for every time you get out of the house and try your best, you’ll find some success. If you make a goal of “In my 40th year, I’m going to try four things that I’ve always wanted to try and never did before, and maybe I’ll meet some cool new people,” that’s a pretty cool goal. That’s enough.

Right now, you are working way too hard on this un-friendable, inaccessible dude who won’t even give you his phone number. You are setting yourself a thankless, impossible task, violating all kinds of boundaries, jeopardizing your career, and pulling your entire life out of whack to chase it. You asked me for help, and my help is: Stop. Stop and do anything else with your time. There is still time to correct course, to seek help for the things you struggle with, to channel your enthusiasm into healthier places, and to work on building more reciprocal and rewarding relationships with your community and people around you. If your mentor decides he does want to grab lunch someday? He knows where to find you, and you can break bread then knowing that he came because he wanted to and not ’cause you dragged him there over the spectre of his friend.

And hi, for everyone reading, if there is a friendship or other relationship that makes you feel like a pair of mismatched socks, what if you stopped trying so hard to make it work or fix it? Stop coaxing, stop auditioning, stop trying to convince people of your awesomeness, do other things with your time, see where you are. 2019 is a good time for trying new stuff. ❤