Scarleteen

So this isn't the first time I've been in this situation, but every time is different, and I could use some 3rd party advice! Thank you!

Just a preface:
I'm a young lady in my early-mid 20s. I've been in two serious relationships, but have also had 3 instances of unrequited love, where I have told other men my feelings and have gotten rejected every time. Most recent was last year, and it really sucked! So I'm a little (lot) scared.

Basically I have a friend, we'll call him "S", that a friend of mine (we'll call her "E") and his introduced me to (as a set up, but I don't think he gets that). He's in his late 20s and has never been in a relationship before. We met in February, and have seen each other about 4 times, but almost always in a group with other friends. One of those times, when we were meeting a mutual friend an hour away, we carpooled together, just the two of us, and he also invited me into his house to show me an art project he was working on (we both have a similar art hobby of making costumes and props). When I left, we shared a sweet but somewhat awkward hug and he seemed to keep continuing light conversation as to distract or keep talking to me.

Not long after that event, I talked to our mutual friend, E, about this, the one that introduced me, and she flat out asked him if he had any feelings for me. At the time, he said he didn't.

Fast-forward 4 months, and we haven't seen each other in person. But we've texted almost every day, often times with him starting the conversations. Usually it relates to our shared hobby, but we also often discuss our family and work lives, sharing details about how we feel in circumstances in these settings. We also often share music and pictures of what we're working on. We're both preparing for a fan convention taking place next weekend, which I will definitely see him at. He's offered to help me with my project and is creating an extra prop for me, which he offered to do, without me asking.
S seems to constantly be busy on weekends with his job, which he works lots of overtime hours for. I haven't specifically invited him to do anything with me, but I try and drop hints about "we should do [activity] sometime", and I feel like he's not getting them.

When we've chatted, we do joke, and he will often use or emojis. I don't know if that means anything, but from a guy, I kinda take that as flirty. I reciprocate that as well, and try to flirt back or compliment him.

Anyways, I have feelings for S, and I'm super anxious about seeing him next weekend. Part of me wants to tell him how I feel, after seeing how our next time together goes, but I'm also apprehensive because I don't want to ruin our friendship or feel stupid for telling him after knowing he didn't have feelings for me months ago.

Not sure what to do. Sorry that's so long. It's complicated. I really enjoy talking to him and being around him, and would like to see him more. Not sure if his feelings on me have changed or will change, but I'm feeling very conflicted!

Hey sugar23

I'm sorry you're feeling so conflicted! It sounds like you really value the friendship of this person, and I get how hard it can be when you want more and the other person might not.

I say might not because there are a couple of things here that make me cautious. Firstly, the fact that he told your friend a while back that he didn't feel that way. Yes, people's feelings can sometimes grow and change but it's not something you can wait for just-in-case. Secondly, you say you've suggested activities and nothing has come of that. It sucks, I know, but the safest thing is usually to take "maybe", or silence as a no.

Obviously, I can't read this person's mind, but I think it's best to be prepared for the eventuality that this is not a romantic thing for him. It sounds like he thinks you're awesome, and cares about you enough to help you with your project and that's great! Friendships are really, super-important and often last longer than romantic relationships.

If you need, I think you can ask him - once - if he is interested in hanging out outside of the conventions and events you usually see eachother, and if so whether as a date thing or as a friend thing. If the answer is anything other than a big YES it's time to stop pursuing that. Does that make sense?

It's up to you how much you want to keep in contact if it turns out you want different things. Maybe you need some space, maybe you can maintain this friendship whilst pulling back a little on the emotional investment so you have some to spare for the other things and people in your life.

Do you want to talk any more about the feelings of rejection that you've been dealing with already? Is there anything else we can help out with?