Dear Captain Awkward,
So, this friend is someone I’ve known for nearly a decade. We went to college together, we were roommates during and after college together, we’ve collaborated on work together, we hang out weekly, we have certain holidays we spend with each other . . . that sort of thing. We’ve had our ups and downs, but arguably our relationship with each other is the best it’s ever been.
Problem is this: friend is very unhappy about her dating life. She has never had a significant other in all the time I’ve known her and has barely gone on dates — not for lack of interest in having either, but from a seeming dearth of potential partners. This is inexplicable to me, as she’s not a bad catch in many departments and can be a very likable, funny, cool person with undeniable talent, but the fact remains that she has been unhappily single in all the time I’ve known her. And yes, “unhappily single” are her own words, not mine.
Many of our mutual friends have gotten married in the past few years, which only reinforces her feeling that there’s something wrong with her. While I’d say that priorities re:hanging out probably do change after getting married, I can’t help but agree that many of these friends didn’t really stay in touch or spare her much consideration even after the honeymoon phase was over, which was kind of crappy of them. She says she feels abandoned and like she’s still in high school, which is a hell of a thing for someone in their late twenties to feel about themselves.
Basically, Friend feels really bad about herself and depressed about her life situation, and anger and unhappiness about this have led to some friction and oversensitivity on her part to the point where I don’t even hold hands with my boyfriend around her (yes, she has complained about this at times). Since I didn’t date or have relationships until comparatively late in our friendship, I think she always assumed that she at least had one friend that wouldn’t leave her for a relationship (she said as much once) and initially reacted badly to my boyfriend for that reason. She has since apologized, I try to accommodate her feelings within reason, and she’s warmed up slightly to my S.O., but it’s a little stressful at times. We’ve commiserated in the past about the weirdness of dating, the unhelpfulness of people telling you to be happy on your own when you actually WANT to be with someone, and so on, so it’s not like we don’t talk about the situation.
Here’s the problem — or, more accurately, the new problem: boyfriend and I just had the Talk last week, and we’re planning on getting married within the next two years. We decided on doing the formal proposal thing around Christmas while visiting my family. I’ve told only one person, an old friend who is hugely supportive of us tying the knot. The issue is how and when to inform Friend about our engagement — she’s one of my closest people and would expect to be let in on the secret as soon as possible, and indeed would be hurt not to be told relatively soon (related things have been an issue in the past). At the same time, I’m literally her last friend to get married, and I’m worried this will begin another fugue where she feels terrible about herself.
How do I break the news compassionately? Or am I just being a wiener?
Dear Ms. Wiener:
You’re not being a wiener. You have ample evidence that your good news may be met with ill will, and the fact that you are dreading this so far in advance of when it needs to be said is a sign that this friendship is a bumpy one.
However, you are not getting married AT her. Your romantic happiness does not subtract from the sum total of happiness available to others. And her feelings about your happy announcement are very much her own. If she reacts badly to your news, those are her feelings that she is having, not something you did to her or need to apologize for. Not one bit.
Jealousy happens. We get rejected from the film festival and someone we dislike gets in and for a second it’s easy to see it as something they are doing to spite us. Another common problem I see in advice columns is people who are struggling with infertility having trouble being happy for friends and family who get pregnant. Burning hot jealousy and shame and resentment and bitterness is real. But feelings and behavior are two separate things. We can sit with our feelings and respect them, and we can also decide how we behave toward others. And the correct thing to do, even when you feel jealousy and bitterness, is to show happiness for your friends when they are happy and lucky. If you can’t do a minimum amount of “Congratulations!“, absent yourself from the conversation until you can.* If your response to “Guess what, I’m getting married!” is “Cue the sadness spiral of sadness! I demand that you deal with my pain now, at length and in detail” you are the one who is acting like a wiener.
I also think that friends with happier news can be sensitive to their friends’ situations, as you are trying to be.
My advice is to tell her when there is an official proposal/engagement the exact same way you would tell friends you expect to be happy for you and let her feelings be her feelings. Perhaps send an email to her and several other close friends at the same time and don’t put a lot of time into singling her out for a serious talk.
If she gets angry at you for announcing your engagement, you are well within rights to say “I am not getting married AT you, can you try to be happy for me?” and bail on the conversation for a bit. I have a lot of anecdata that suggests that close friendships survive (gasp!) marriage, but I have a theory that those are the ones where people don’t treat the other friend’s marriage as a referendum on the friendship or anything but “I wanted to marry this dude and also be your friend, still.” It’s not like you could solve her problems by not getting married, right? Or that it would be worth it to not get married because it would make her feel a tiny bit better about herself (but still hate herself, really)? You’re gonna do it, so do it totally without apology.
I hope she gets some therapy and treats her depression like the real soul-sucking demon that it is, and I hope you guys remain close, but that’s not something that you can control with the announcement of your nuptials. Just tell her in the same chill way you tell everyone and hope for the best.
*We can’t always control our reactions or predict how news will land with us. Fortunately any good friend worth their salt should be able to roll with an honest: “Congratulations! I am happy for you, but this news is hitting some of my own issues strangely and I need a second to pull myself together. I’ll circle back to celebrating in a bit when I feel less weird.” If you need to hide someone’s social media feed because it’s All Baby or All Wedding, All The Time that is also a totally understandable way of taking care of yourself. You don’t have to lie, you just have to not vomit your despair all over your friends at their happy moments.