How to keep offering support to someone in grief

Question

A bit of history to explain our current relationship:

I met a person recently over a dating app, talked a bit and then met for a date which ended just as a friendly chat, and due to distancing there wasn't a chance to try to see if there's any interest of getting closer than just friends. Later we talked about having a nice time and I mentioned that I would like to continue the friendship and also something more. Answer was that it isn't a good time since they ended their previous relationship recently.

For few more weeks we chatted, shared memes and projects we're working on, and decided to spend more time together, having few coffees and walking around the city for hours to just avoid groups of people.

We can't just spontaneously meet since we live a bit over an hour drive away and they fill their schedule in advance a lot. (I tried to organize the last meet for "the next day" but it was rejected for that reason, and they imediately found an option that works, so it doesn't seem like just an excuse to reject everything)

I had some plans for next weekend so we said we'll talk later about some other time, and then the actual situation started

Their childhood pet died. I offered my condolences, and let them know I'm available for them, to which the reply is that they're holding ok, they'll just focus on the work, and they changed the topic to me. After a few more messages I asked if they want to meet in few days, since when the same thing happened to me I wanted some company, and the answer was no, they don't want anyone around now. After that I've left them alone and there was no contact back.

In the mean time they adopted another pet from a shelter which sadly passed away just few days later. I saw it on social media, left "reacts" there but here's where I'm stuck.

How to continue the conversation with my friend? I thought I'd offer my condolences again, but I don't know what to say that wouldn't be exactly the same as last time. Then I thought of just starting a conversation like nothing happened, send some memes, ask them how they are, but I thought that might just be ignoring the situation and seem cold, so I went here to ask the question.

My main goal is to let them know I'm still there for them, that we can talk about anything if they want, but also that if they want to be let alone I can do that, I'm just not sure if they don't want to meet people, or also not talk with them too.

Second goal is to do that in a way that doesn't seem like I'm overanalizing the whole situation and focusing too much since it's just a few month old friendship where we met twice. (I know I am doing it, but I don't want it to be obvious)

Answer 1

It's easy to overthink these kind of situations of a new friendship with the added stake of possible future relationship. It's also difficult to imagine what feels someone in grief when you've not been there yourself, and even so, we all react differently under these circumstances.

Some people will like to talk to you about their feelings, some will try to isolate, some will expect you to cheer them up, and it's near impossible to guess without knowing that person extremely well, which you may not.

Most of what I did with people in grief around me was just to be there and let them know I could be there if they needed anything. Some of them found relief in explaining they felt guilt, with me generally explaining this was unnecessary burden.

On the other hand, I've been depressed for other reasons and know what it's like to have friends that are sending you completely off comments, so I could give you a tip or two in avoiding to be cheerful when the person wants to go dark and vice versa.

If your primary mean of communication is text, I would try to guess as early as possible what part to play. This is literally what the questions like "How are you doing?" are going to be effective in that, or if you want to be specific, you can also mention the incident "I saw in xxx media your pet died..." but again try to be in a listening stance by precising "Tell me if you need anything" or similar. By opening the conversation toward them instead of telling how you feel about that you invite them to lead conversation toward the end they would like, or end it if they would like.

If you feel like you're repeating yourself, well people repeat themselves everyday when they say hi, so opening the conversation the same could be equally adequate. It's probably different for your interlocutor this time and there is no reason they will repeat the whole conversation a second time.

I would not think it is a very good idea that you try to open the conversation making "customized" condolences because this is usually how you would make comments that aren't very comforting. Even saying "Two times in a row, that must feel terrible" isn't so good, because you could make feel guilty a person that actually feels not that bad, and more importantly because it makes a parallel that doesn't exist since we love every pet differently.

In any case if you don't want to sound too cold, which is your objective, you could try to setup a voice call (or meet in person if that is feasible) as it will always be easier to vehicle emotions and empathy this way.