Should I stick a fork in this relationship?

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I am not a very social person. Some would say I'm socially awkward, but I'd say I just can't figure out people. If the pressure is off and I am comfortable. I can appear "normal" and interact, but for the most part finding people to befriend has proven traumatic to say the least, and COVID has only made this that much more difficult.

I met a woman near my age about two years ago. She worked at a client's, and I regularly talked to her. She was very easygoing and fun to talk to, but I never even thought about approaching her for anything beyond our business relationship. For whatever reason, we ended up texting each other, and that led to flirting and some rather interesting texts. We eventually made arrangements to have a date or two and things went well. If anything, she was way more aggressive than I was, and I kind of felt I needed that. It was a little intimidating to have her come on so strong but I thought I could keep things moving forward, but slowly.

I was recovering from a divorce that happened five or six years ago. I was eager to pursue a relationship with this new person, but I was trying to be cautious for both our sakes. Eventually she felt I couldn't give her what she wanted fast enough, and then an old flame showed up in her life. She had reservations about this guy showing up. We remained friends, talked semi-regularly, and even flirted a number of times, leaving me to believe the interest was still there. She moved in with this old flame (out of state) where things went south, and after half a year she came back here. She contacted me, detailing all the horrible things she went through with this guy and hinting that she'd be available to restart our relationship – or at least thats how I interpreted it.

Cut to four months later and I am confused and left isolated. She says she has interest, admits she should probably move forward with me, but she's giving me mixed signals - ghosting me, saying she's not ready for dating, then flirting again. She has a young daughter that she says takes up most of her time and energy. I have said I'd love to help her and be around her and her daughter if that would help take some strain off of her, but I still get nothing but mixed signals. I came straight out and asked her if we could see each other, and if she was even still interested anymore. She didn’t give me any definitive answers either way, but did admit "she did want me" and that "she should probably just follow her mother's advice and see me" – but nothing has happened. I am left confused and alone, both embarrassed and empty. We are at the point now where we talk, we flirt, I ask to see her and she says "maybe," and then I don't hear a peep from her. I'm at the point now where I just don't want to even ask anymore. I feel like whatever potential this relationship had is now just muddled with poor communication, mixed signals, and ruined excitement. Should I just swallow my pride and stick a fork in this (and let her know how disappointed I am), or just ignore the entire situation and move on? I am dying emotionally from isolation, and this situation has promise, but is causing me a lot of anxiety and confusion.

– Promise


"I feel like whatever potential this relationship had is now just muddled with poor communication, mixed signals, and ruined excitement."

Well said.

This relationship isn't happening, so there's no reason to wait around. Maybe she still has feelings for you, but she's not ready to do anything about them. That's unfortunate, but it happens. Timing isn't everything, but it's important.

You don't like mixed messages, so let her know where you are with this. You're going to stop reaching out so you can figure out what's next. Tell her you'll contact her if you're ready for a platonic relationship. The end.

She might try to bargain with you – she likes your attention – but you can counter by asking what she wants. I'm guessing she doesn't know, and that's something she has to figure out on her own.

You talk about pride and embarrassment. I want you to know that many of us have had unrequited crushes, waited around for someone to like us, and given someone the benefit of the doubt when they seem lukewarm about showing up. It's all part of love and dating. It's almost impossible to avoid hurt feelings and lessons.

Please know that when I read this letter, I feel hopeful. I see a person who's capable of courtship, flirting, communication, and love. You might understand people – and yourself – better than you think.

That said, if you're concerned about what you mentioned in that first paragraph, look into help – therapy, somewhere to process confusion, new ways to socialize and build community, etc. But know that this letter is like a lot of other letters. I hope that's validating.

You have more promise than this relationship. Let yourself move on.

– Meredith

Readers? End it? Advice for someone who's having trouble socializing right now?