Make a move or wait?

[TH Anonymous]

[SIZE="a"]I’m generally okay with being single for now. But, I’ve recently started thinking more long term and think maybe I do want to get married and have children one day. But I never cared much for dating and didn’t think about it. The last relationship I had was when I was 15-16- over 10 years ago! I’ve had some people take interest me since then but it was often for casual reasons or maybe I didn’t like them/felt ready so it never went anywhere. I also have a tendency to go along with things and lack assertiveness, as well as a possible tendency to get ‘obsessed’ and like to daydream/imagine things. I’ve also had problems with insecurity and clinginess which was what ended my last relationship. I’d like to think I’d do better this time but not sure.

Recently, a particular guy has been on my mind. We were in the same high school (not class) and caught the same bus (this was nearly 10 years ago). I remember kind of liking him (not a huge crush or anything but generally noticing him) back then but I didn’t have friends/felt depressed and never got to know him. But I remember chatting to him once or twice and he made me laugh about something. We connected on social media a while back, but aside from reciprocal birthday wishes, neither of us talk to each other. I have noticed that he has previously liked some of my profile pictures and I’ve liked some of his too. Not that that means much though.

The thing is though, I feel like we’ve gone in different directions. Over the last few years, he’s got a job related to his degree and has been looking after himself and working out. But for me, I’ve put on weight (camera angles and filters don’t show that so I feel a bit misleading) and am unemployed. I am looking to get healthier and lose some weight and am applying for jobs and trying to find out exactly what I want to do with my life. I’ve often been called ‘boring’ in the past too. I don’t know whether it’s worth making a move within the next few months (my birthday is next month and failing that there’s always valentine’s day next year, so both are options for talking to him, though I wonder if he’ll think it’s a wind up since I barely talk to others on social media) or leaving it until I feel better/am in a better position e.g. happier with my weight and possibly working? But then I’m worried that I don’t know when that will be and maybe by the time that happens, he might not be single. Maybe I should just review the situation/how I feel every few months?

I barely notice guys to begin with, and when they approach me I tend to turn them down, and I don’t go to bars or have much of a social life. I do worry that this is all in my mind or maybe I might be lonely or something. I generally prefer getting to know someone first and then letting feelings develop so the fact this guy is singled out in my mind feels a bit concerning to me. I don’t even know if we have compatible life goals e.g. I know one day he wants to move abroad and yet I can’t see me doing that, at least not permanently anyway, and that makes me question whether I should even try to approach him in the first place. I wouldn’t really know how to approach him aside from just randomly coming out with how I like him but that’s another thread for another time

I don’t even know if I’m ready/in a position to date. I may be overthinking this but I genuinely don’t know how to approach dating/relationships and it’s weird now I have a certain someone on my mind. So yeah, don’t know if I should make a move or just wait until I’m in a better position or something. I’m afraid of being clingy and messing it up and yet I’m also afraid of missing out. And yet maybe a few months down the line, I’ll laugh at this and think it was nothing, just in my head. I’m just full of contradictions lol.

Any help/advice would be appreciated! [/size]

Honestly, before "making a move" I would just try and talk to him more. Build up that friendship and see where it goes for both of you. It's hard to flat-out make a move with someone you don't have much of a relationship with (currently); it would come out of the blue and you probably won't get the response you are hoping for. But there's nothing wrong with becoming more interested in talking to him. You could message him and ask how he's doing, or if a meme or something made you think of him you could share it and tag him.

About where y'all respectively are in life: it's okay not to have everything figured out. It can seem intimidating to approach a person who has all their stuff together (seemingly), but you're taking concrete steps to move forward and better yourself, and that definitely counts for something. It makes a difference.

Good luck and PM me if you need anything.

[Mallika]

Hi there,

Thanks for reaching out!! I think in several aspects I went through what you're going through recently, so I might be in a position to advise.

It is natural to want to reach out to someone yet feel like we're "not there yet" with our own progress in our life's ventures like career, etc. But remember, relationships with people is one thing, while our stage of progress in our life journey is another. Yes, the two are linked in several ways, but remember that not everyone can have everything "figured out" at all times in life. Everyone operates on their own timeline. This shouldn't stop you from seeking romantic interest.

Like you, recently I was waiting to ask out someone who is based in the US but I was dependent on the outcome of my applications to some schools in the US, thinking that I'll message him only once I get the confirmation that I'll be moving to the US. But I wouldn't know that until around 6 months later. I didn't want to ask him out before I knew this, because I thought it might increase my chances of being rejected. But then again, I didn't want to wait that long because he might not be single anymore. So I decided to do something along the lines of what Eli said - I sent a DM that expressed my interest but at the same time didn't demand commitment so he wouldn't feel pressurised or creeped out. I don't know him personally because I met him through a mutual Facebook group, but at least this guy hasn't rejected me yet and is probably/hopefully thinking over my message because I sent it only recently. You are at an advantage for having known the guy you like personally, though you've had limited interaction. Knowing someone in person makes a difference!

Since you know him, it might be a good idea to start off with something casual. Since you guys don't talk much, he might even get the hint that you are showing interest, which is good. If you straight-up say that you have a crush on him, it might scare him off. So perhaps you could share a meme, or a puzzle question or something fun and build up the conversation from there. Are you into any sort of video games or games in general? My best friend often plays online chess with his pals, where each person creates a character. Another example is something called an "escape room", which is a mystery-based online game where you work in a team to solve clues. You can gather a couple of friends and ask him to join if he's interested. That's a way of also getting some interaction with him.

If you're comfortable with this, you can even reach out to him with a genuine question. Perhaps you could ask him about advice on something (e.g. maybe about the work he does, or something). Of course, it is better that you're reaching out to him with a genuine curiosity about the question you're asking, otherwise it would seem quite pretentious that you're doing this only to get his attention. But if you do think of something you'd like to learn/ask him about, that's a great way to also start a conversation. Plus, you also get some pointers from him about your question.

I don't think you need to wait to reach out to him. Yes, you might want to wait until you tell him about how you feel. But don't let anything stop you from starting a conversation. It all begins from there

Good luck! Feel free to DM me if you have any questions!

[Mallika]

Hi there,

Thanks for reaching out!! I think in several aspects I went through what you're going through recently, so I might be in a position to advise.

It is natural to want to reach out to someone yet feel like we're "not there yet" with our own progress in our life's ventures like career, etc. But remember, relationships with people is one thing, while our stage of progress in our life journey is another. Yes, the two are linked in several ways, but remember that not everyone can have everything "figured out" at all times in life. Everyone operates on their own timeline. This shouldn't stop you from seeking romantic interest.

Like you, recently I was waiting to ask out someone who is based in the US but I was dependent on the outcome of my applications to some schools in the US, thinking that I'll message him only once I get the confirmation that I'll be moving to the US. But I wouldn't know that until around 6 months later. I didn't want to ask him out before I knew this, because I thought it might increase my chances of being rejected. But then again, I didn't want to wait that long because he might not be single anymore. So I decided to do something along the lines of what Eli said - I sent a DM that expressed my interest but at the same time didn't demand commitment from his end so he wouldn't feel pressurised. I'm still waiting for his reply (well, it's not like I know him personally, I met him through a mutual Facebook group + I sent him this only recently) but at least he didn't reject me yet.

I think you could do the same. Since you know this guy, it might be a good idea to start off with something casual. Since you guys don't talk much, he might even get the hint that you are showing interest, which is good. If you straight-up say that you have a crush on him, it might scare him off. So perhaps you could share a meme, or a puzzle question or something fun and build up the conversation from there. Are you into any sort of video games or games in general? My best friend often plays online chess with his pals, where each person creates a character. Another example is something called an "escape room", which is a mystery-based online game where you work in a team to solve clues. You can gather a couple of friends and ask him to join if he's interested. That's a way of also getting some interaction with him.

If you're comfortable with this, you can even reach out to him with a genuine question. Perhaps you could ask him about advice on something (e.g. maybe about the work he does, or something). Of course, it is better that you're reaching out to him with a genuine curiosity about the question you're asking, otherwise it would seem quite pretentious that you're doing this only to get his attention. But if you do think of something you'd like to learn/ask him about, that's a great way to also start a conversation. Plus, you also get some pointers from him about your question.

I don't think you need to wait to reach out to him. Yes, you might want to wait until you tell him about how you feel. But don't let anything stop you from starting a conversation. It all begins from there

Good luck! Feel free to DM me if you have any questions!