Should I, or should I not, be dating? feeling hopeless but not acting hopeless

I'm a 31 year old graphic designer/musician, diabetic, celiacs disease, in a lot of debt I haven't been able to pay off (medical, student loans), living with family, working a dead end job for over three years with no review/raise in sight. My degree is obsolete, currently exploring new career paths. All of my friends have significant others, getting married, having kids, buying houses, etc... I don't necessarily feel pressure from those things, it's more that I'm barely getting by and it crushes my self-esteem. My last relationship was quite bad. Knew each other since we were kids, I was by her side for every moment of breast cancer, her treatment was successful. I was with her before during and after cancer and I was treated bad the whole time. I rolled with the punches because I'm aware of what chemo can do to a person, I was there when my younger brother went through it. I broke up with her because how she treated me had nothing to do with cancer.

Been feeling kinda hopeless for some time now, but I do not act hopeless. I push forward to research and apply to new jobs, exercise regularly, creative pursuits that make me happy, and sometimes I wish I wasn't doing these things by myself, but every so often the reality of my situation sets in and I get discouraged. I have friends who always encourage me, even when family does not. I keep feeling that I shouldn't bother trying to meet someone, I feel that I can't afford a girlfriend. I often get that "why are you single?" or friends trying to set up. I've also been told that I'm bad at getting the hint of interest because I never assume. Tried Okcupid for a while, went on a date, communicated with several ladies, but nowhere I'm patient. Most of them kinda bailed once it was revealed that I live at my father's house. A couple months ago I came in contact with someone who was a high match who lives 45min. away, messaged each other for bit. I sorta moved around in the past year and re-evaluated my finances and that "reality" sorta kicked me down again. I told this wonderful person that I just didn't feel confident attempting dating at the moment. She contacted my art page on Facebook and messaged me saying I shouldn't be so hard on myself and that I'm an upstanding guy and that she'd like to be friends. We've hung out a good amount since, we've gone hiking several times, met up for a few drinks, saw a band, got food and attended an art show, etc... I'm starting to really like her. She's quite amazing, we have a lot in common and similar interests; she's very talented and we plan on writing music together in the near future. I can't think of anything cooler than all of that.

What I'm wondering is; Should I pursue or hold off? I feel and hear both sides equally. Maybe I'm just another guy friend to her, maybe she's getting interested? Maybe I should focus elsewhere? I feel I need to back off on isolating myself so much. Just because a lady shows interest, doesn't mean she actually is. I appreciate.

Updates:
I don't really know what "she's cool with" seems to like hangin/talking. I don't really want anyone feeling bad/sorry/pity for me because that can't be attractive and my lack of confidence is probably a turn off, but she initiates conversation and aims and follows through with plans with me. Time will really tell and I am patient. My first mention to her that "i don't feel confident dating" maybe that's a relief to her so that's why she likes to hang out? Why would a lady bother? Time will tell.

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Most Helpful Girl

  • I'm glad that you are actually thinking of what's the impact of having a relationship - the cost, and how it would affect your potential partner in the future. Personally a guy who lives with his parents would cause me to take a step back because in the end I don't want to be the guy's sugar mommy and all that.

    That said, going out and doing fun activities with another person is a step in the right direction. You can use her as a your muse as you try on other things and push yourself out of debt, work on getting a better job and what not. Don't push yourself so hard that if I date I have to ask her to be my girlfriend soon etc etc. Just take it slow and be honest with her.. Have fun cheap dates like going out for coffee and telling her about your day.

    The more you share your insights with a girl, that is a more of an enjoyable date than a fancy expensive dinner but the guy is hooked to his phone. But when I say insights as in, positive thoughts or what not. Don't be a downer like ramble on a woe is me attitude. If there's a problem share it with her and run through her some plans of action you want to pursue to remedy it, and what does she think about it. In the end she would understand why you are taking it slow and take her cues from there.

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What Girls Said 1

  • If she's cool with everything, go for it!

    I understand where you're coming from with everything. I didn't date for a year and didn't even crush on people because I knew I was going through too much and it's not fair to put that on someone else. I think that's a very good idea to stick with. It's better to work on yourself first.

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What Guys Said 1

  • Hey paisan...

    I say go for it. I'm around the same age as you, and I'm also grappling with some of your problems...

    While I don't live at home, I am strapped for cash, and I also constantly get the "Why are you single/Why aren't you dating" sh*t all the time...

    Women aren't cheap, not by a long shot... but still, I have to believe that there's a woman out there who could care less about financial stability, and actually goes for a man of substance...

    It's your job (and mine) to find her.

    Lay it all on the line with this chick... if she goes for it - Great. If not, then she's a "dishrag whore." - Eric, KILLING ZOE

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