Dear Captain Awkward,

I have an awkward social situation that I’m not sure how to handle. It’s been causing me a bit of anxiety, and so I’ve been avoiding dealing with it.

Recently I have had a rash of old friends who I am no longer close with contact me, wanting to either catch up or get together. Some of them I’m happy to have a chat with and tell them about my life and hear all about what they’re up to now, but when they suggest we start hanging out again I feel stressed. The problem is that I simply don’t know how to fit these people into my life now.

For a long time I was very mentally and emotionally unhealthy, and I self medicated with drugs and alcohol a lot and was a bit of a party girl. Right now I’m the healthiest and happiest I’ve ever been, and I can look back on those years with new clarity and insight. I see now that I tended to be drawn to people who were dysfunctional because it allowed me to feel like I had my shit together, even though I really didn’t at all. I’ve done a lot of work on myself since then, and I feel like a lot of the friendships I made at that time in my life are no longer fulfilling to me. I’ve purposely distanced myself from a lot of people, not because I think they’re bad, but because I now find their company totally draining. Hanging out with them became something I did out of a sense of obligation. I felt guilty at first until I realized how much happier and calmer I was without them, and that I now had room in my life to make new friends.

There’s one old friend who won’t give up trying to contact me, who I particularly don’t want to see. We didn’t have a falling out, I just realized that I didn’t really like her anymore due to her rudeness, self centeredness, and flair for the dramatic. I was ok with it when she moved a bit further away and we lost touch for a while. I hadn’t heard from her in a couple years, and I was pretty relieved. She texted me at the start of this year saying she had moved back into town and invited me to her birthday party at a bar. I felt an immediate sense of dread. Since it had been a couple years, I pretended that I got a new number or something and didn’t reply. Maybe that was wrong or short sighted.

A few months later she found me on social media and messaged me “WHEN ARE WE HANGING OUT?!?!” which both terrified and annoyed me. I thought it was a rude way to make contact with someone she hasn’t seen or heard from in years. I felt put on the spot and uncomfortable. It made me want to get together even less. I didn’t reply and hoped she would get the hint. She didn’t.

A few weeks ago she found me on another platform and commented on one of my posts “Hey! Let’s hang out!!!”. I didn’t reply and haven’t posted on that platform since. This morning I woke up to a direct message from her saying “(my name)?!?!”

I think at this point I need to be direct because she is not getting the hint and it would be cruel of me to continue this tactic, but I really have no clue what to say. I’m not mad at her, we didn’t have a falling out and there’s not really a specific instance that made me not want to be friends anymore. I don’t want to be hurtful. I’ve been on the other side, attempting to reconnect with someone and realizing that they had no interest. It sucked but I got the hint and let them go. For me, this friendship is over.

What do I say?

Sincerely,

Chronic Avoidance

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Dear Captain,

I have a colleague, “Peter”, who I’ve known for several years. We first worked together at a festival, and added each other on facebook/phone for organisational reasons, as he was the crew leader. Over time we have become friends, although I do see him as more of a colleague as he is 20 years older than me with a kid, and I’m a student. I worked with Peter again this year, and during the festival he split with his girlfriend. Naturally he was upset, and I was sympathetic – at first.

Recently, he has been pestering me on social media, and on the phone when I ignore his messages. I shouldn’t ignore him, but he frequently sends me random unsolicited updates on his life/ weirdly personal accounts of his break up, often at 2am, and I don’t know how to respond. Sometimes I will commiserate, but then he will turn on me and ask these loaded passive aggressive questions like “you really ok with this?” or “am I being obtuse”, so I have stopped responding as I don’t have the time or emotional energy to deal with him right now.

I think he is just looking for a friendly ear, but I’m struggling to deal with someone who is so emotionally vulnerable and so different from me. When I do respond, we get our wires crossed, so I try and keep my replies neutral. For example, he had been trying to recruit my young best friend to his crew, and even after I said she wasn’t interested multiple times, he added her and starting talking to her on social media. I got annoyed at him over boundaries and he got in this huge strop about how he could do what he liked. Then he eventually apologised, but the rift keeps widening.

Peter constantly questions how deep our friendship really is, and to clarify, I have always seen him as a friendly work colleague. From my point of view, him pouring out all these emotions on to me seems very strange, as surely he must have closer confidantes his own age? I probably sound quite cold, but I don’t think he should be discussing the legal issues and horrible drama of his break up with me.

I want to maintain our good working relationship, but don’t know how I can enforce boundaries, particularly on social media. Help!

She/her pronouns please. 

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Dear Captain Awkward:

Please help captain! (I really struggled getting my letter to around 400words – there is a lot more detail if you need it 😊)

My brother-in-law ‘Hector’ is 36 and ‘Agnes’ is his first ‘girlfriend’. I’d known Agnes for a few years before setting her up with Hector– she’s now 40 and her only previous relationship was when she was a teenager.

Over the years I’ve known her she had displayed a lot of questionable behaviour e.g. stalking guys she was interested in, obsessively stalking old friends on social media and do things like go through people’s drawers and medicine cabinets and take photos which she’d share with her mother. I’d overlooked these things as she was fun company (apart from the strangeness) and I don’t have that many friends.

So basically I set my dysfunctional brother in law up with my dysfunctional friend and now I’m suffering consequences, and now it’s affecting Christmas.

My husband and I alternated Christmas – one year at my parents and the next at his. Agnes now refuses to spend Christmas day at his parents’ as she ‘has a niece’ (her ‘weapon’) and so spends every Christmas day with her family. She hates my in-laws – she refuses to let them into her house whilst she is there, and sulks whenever she is in a room with them.

So, 2 years ago my husband and I decided to host Christmas, either on Christmas Eve, or Boxing Day (thereby letting her spend Christmas day with her family). This worked well. However, this must have been going too well (as Agnes lives off drama) and so when I asked about Christmas (at this point we were relatively close and messaged each other every day) she told me that it was all arranged and that she and Hector were spending Christmas Eve with her family and that they had made arrangements to go to the in-laws on 23rd December.

I replied saying that I was upset that my husband and I were not asked. Since then I have not heard from her (this was back in August).

My husband and I have since decided to go ahead as we would have done, and are hosting on Christmas Eve –we invited Hector and Agnes, and the invitation was declined. However, I’m still upset and brooding about this. If she’d have just said ‘oh my sister has invited us to a meal on Christmas Eve’ I’d have given options and worked around her on the dates – but the fact that they’d just arranged it all without us… just hurts.

I was hoping for a script or some advice on how to handle this difficult relationship going forward?

Many Thanks

Regretful matchmaker

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Hi,

I’m a 30 year old man with a family of four, and I’m a member of a church community of about 140 people, 80 active members. I’ve been mostly inactive for over 10 years, but go to things occasionally. My parents have been active my whole life, up until five years ago my mother got very ill. My father has kept going to church and doing activities, up until the last year. His reason was that he was sick of people asking how my mother was doing and never asking him how he was doing, and has stopped attending.

Initially, I didn’t think much of this and felt my father’s reasoning sounded a bit selfish. My wife has pointed out that it was our community’s way of indirectly asking how he is doing and showing they care. I had experienced some of the same, but didn’t think much of it, until I started getting active again in the last couple months, and honestly, I’m starting to see what my dad means.

Week to week, my mother’s health does not change. Every couple months she has an episode of some kind and recovers afterwards. But that is the question, every time single time I attend an event, multiple times per event. It is surprisingly grating over time. I feel like it would rude/passive to aggressive to add, “I’m doing fine by the way” or “She’s not getting better, stop asking.” I do think it’s coming from a good place, but I’m seriously thinking about attending a church that doesn’t know my mother.

Thanks,

Random Dude

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Dear Captain,

Since I moved in with my sister three months ago, I’ve been….missing things. Things that are important to me, things I wouldn’t normally lose. My boyfriend’s $700 camera. My only/favorite pair of sunglasses. An Adderall prescription.

I’ve complained about this to my sister. I’ve wondered aloud to her if our third roommate has been going in my room, or if one of the friends passing through isn’t as trustworthy as we think. I’ve talked to her about how weird it makes me feel to worry that people are in my room when I’m gone, about how much I hate to distrust anyone, about how I try to convince myself that there’s some innocent explanation I’m not seeing. It did not occur to me that she could have anything at all to do with the situation–I trusted her completely. Until the day before yesterday.

The day before yesterday, we found the camera. Well, I shouldn’t say we. She found it. We weren’t even looking for it. We were trying to find the bottle of adderall. The adderall had been missing for days, the camera had been missing for months. Within minutes of us starting the adderall search, she opened up the cabinet under the silverware drawer, moved the paper napkins, and said, “Hey, is *this* your boyfriend’s camera that’s been missing so long?” It was.

Normally that wouldn’t seem suspicious to me, just weird that it showed up in a place that neither I nor my boyfriend would ever put it, and weird that I’d been using the cabinet for months without noticing the camera. But I had just watched the episode of Mad Men where [spoiler!] Sally steals the $5 from Grandpa Gene and then “finds” the money when he makes a bigger deal of it than she had anticipated.

Pretty soon she was asking all these questions…didn’t my boyfriend already get a replacement? What was he gonna do with this one now that we found it? Did he want to sell it? It probably wasn’t worth as much as he paid for it, the case wasn’t made of great material, good but not great, could she buy it for a couple hundred dollars?

It all made me so, so uncomfortable.

And today I remembered that around the time my sunglasses went missing, my sister bought me a new pair. They were old-fashioned and had that tortoiseshell look, like the ones I lost, but they were cheap and much too narrow for my wide face. (Part of the reason I’d been so bugged by losing the first pair is that finding cute wide-framed glasses has always been difficult for me, and I’d spent a fair bit of money when I finally found a pair I liked.) Now that interaction seems tinged with weirdness to me…like, was she trying to make up for taking or breaking the sunglasses in the first place?

And the Adderall never showed up, which is such a huge hassle.

I don’t know. Obviously none of this is 100% proof that she took these things (or that anyone did! maybe I just lost them!). It would be so much easier if I knew for sure….even if I knew for sure that she did it, I wouldn’t be super mad. But I would feel justified in taking action to move out and protect myself. As it is, I’m stuck in a state of uncertainty, having to live with someone I don’t totally trust, and feeling guilty for being distrustful when she might be totally innocent. In fact, the only things that make me feel suspicious of her, are good things she did–finding the camera, buying new glasses.

Help me, Captain! Did she do it? And, given that you probably can’t answer that, how do I live with this doubt without being unfair to her or myself?

Signed,

Lina McLaidlaw

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Dear Captain Awkward,

I’ve been dating this guy for 3 months now. He has this pattern of disappearing for a couple of days and then come back. At the beginning he was all super flirty on text and showered me with compliments and sent each other snaps and nudes and said all the sweet things like he wants to treat me like a princess and make me his. Lowkey I knew he was a fuckboy* because most of the time he wanted to sext and talk about fucking me. He said he wasn’t looking for a relationship but if we become more than something then sure but if we don’t then we continue being friends. I came out of a 4 year relationship couple of months ago so I have been out of the dating game for too long and I moved in here to California from a different country so the concept of dating is way here is new to me. He was showing all signs of “fuckboy*” but my mind ignored it and I got led on and I started to get feelings for him. I know, you must be thinking if I knew he was a fuckboy* the how the hell did I started to like him?

Well, first of all he is really charming and good looking. He is really smart and does all the gentleman things like open the door for me and pays for the food. He actually seems like a genuine good person when I’m with him. I forget every annoying stuff and red flags when I spend time with him.

I realized our relationship will not go anywhere and he will continue to play with me. Once I told him that I had feelings for him and this is getting too much for
me so I’m gonna end the “friends with benefits” thing and remain friends and he gave a simple response “okay your choice.” After 2 weeks he hit me up on snapchat after he saw a selfie of mine and said he wants to come over to my house in the weekend. I couldn’t say no. We had an amazing time and after that he ghosted on me again. He is emotionally unavailable and does not share much about his life. I want to end it with him but I’m too weak to do it. Every time I pull back, he then wants to chase me. recently I texted him ” are you ghosting on me or something going on with u?” then he replied with ” i’m just damn busy :/” .

I’m really confused what he actually wants. If he doesn’t like me anymore then why doesn’t he just tell me or stop texting me? The relationship is hurting me. I don’t blast him with lots of texts nor do I nag. I always try to stay civil and calm even when i’m hurt by him. I’m having a hard time opening up to him of what exactly I feel. I wanted to take the relationship to another level and spend more time with him getting to know him. I wanted him to be my boyfriend. But I didn’t demand it. I did not expect anything in return when I told him I liked him. Because I can’t force him to like me back.
What should I do Captain Awkward? Even though I make myself busy with things. But I can’t seem to not cut him out of my life for good.

Sincerely Confused

*Fuckboy = the letter writer is using it as a term to describe a man who is unreliable and untrustworthy around sex  or “Someone who’s distant but still craves attention.” It also has a history as a descriptor of prison rape victims and attaching men who aren’t traditionally masculine and is therefore a word we’re not going to use anymore at CaptainAwkward.com enterprises. I’m not telling anyone they can’t ever use it, but I’m going to personally stop. Not least because I am a big ol’ white lady and “well it’s more complex than that in AAVE” isn’t really the hill I want to die on in my comments section. Not every word that exists is an ok word for me. Cool? Cool.

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Putting this behind a cut given the “Guy In Your Office Who Gives Weird Backrubs And Ends Every Sentence With ‘That’s What She Said’ Is Totally #IBelieveYou About Your #MeToo Social Media Posts” and “Pretty Much Every Movie You Loved In The 1990s Is Now Kinda Gross To Think About” week we’ve had.

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