Yeah, date women you’re not sure about it- just don’t be a jerk if it doesn’t work out. Even if nothing else comes of it, it’s still good practice at dating, and without much pressure.
Maybe don’t ask both of them out at once though, that one rarely works.
Correct. To repeat what’s been said several dozen times in this thread - DO NOT ATTEMPT TO DATE PEOPLE YOU ALREADY HAVE A RELATIONSHIP WITH.
No.
Very, very true.
It is a very difficult area. I am very self-deprecating (being British, it comes with the territory). Back when I was doing the online dating thing (personally I found it soul destroying and eventually found someone out there in the real world) a few women said when we decided to stop seeing each other that they were put off by the very low opinion I have of myself. I don’t, it is just that unlike the majority of men in this country I have absolutely no problem with making myself the butt of the joke.
So I can do self-deprecation quite easily, but it wasn’t tailored for the sort of people I was meeting.
When did you start losing weight, and how long have you been at your current weight?
The thread title starts with “Almost 30” but it seems that you lost a few years years of eligibility because of your morbid obesity. How much did you weigh at your heaviest?
I guess it depends on what you mean by mild curiosity. You might not be strongly attracted, but is there a little attraction there? Does either girl seem maybe a little interesting? Does the idea of being in a relationship with either one seem unlikely but possible, or does the idea seem ludicrous?
If there is a little bit of attraction, and the idea of being in a relationship with one doesn’t seem ludicrous, I don’t see anything wrong with asking one of them out for coffee. It would be a good, low-pressure, casual date. You might find that she becomes more attractive when you get to know her better. Or you might find that there really is no spark, in which case you say something about how you enjoyed the date, but don’t feel any chemistry and don’t want to pursue anything further. I don’t see anything wrong with taking a chance and going on a casual date.
However, if both of them are not at all attractive to you and you can’t imagine seriously dating either, then I’d say don’t ask either of them out. I would not be offended if I was asked out for a casual date by someone who was slightly interested. I would be offended if I was asked out by someone who wasn’t interested in me at all and was just using me as practice for women he would actually be interested in.
What, even a mere acquaintance? I don’t think you understand how incestuous this community is. If I cut out everyone I know, there’s not going to be many people left. Within 1 degree of connection I’m probably linked to 90% of women in this age bracket, and within 2 degrees likely the whole town.
Not sure the details are all that relevant, but I was ~250 lbs at my heaviest (plenty fat for an Asian frame) and am about ~180 now, with some seasonal and annual variance (why do I feel like salmon?).
Anyway, I think “average” would be the best description of my body type right now, but I had no better luck when I was skinnier or fatter.
Yeah, exactly. It’s borderline, but if I were completely honest to myself I would say I am at least slightly interested. Guess that’s fair.
Sorry, typo. 190.
Well, I was assuming by “acquaintance” you meant someone with which you share more than just a casual acknowledgment of each other. Still, I’d be wary of asking anyone out that you’ve hung out with in a group before on multiple occasions. And either way - that’s your starting point to asking someone out, “I know we’ve been to the same parties/drum circles/composting events together, but it seems like we’ve never had a chance to talk. It was great getting to know you a little bit better - I’d like to get dinner with you some time. Any chance you’re free next Friday?”
Because of backlash with other friends, or?
Because it clearly hasn’t worked for you. And I would guess that you have a tendency to lead a potential romantic relationship straight down the path to platonic friendship, and this will help prevent you from doing that.
My first impression looking at your profile is you’re a nice looking young man, but you put very little effort into taking care of yourself. Do you ever “clean up” before you ask women out?
Good points.
I bathe regularly and brush my teeth. I shave down to a stubble. What else should I be doing?
I think asking one of them out would be a great idea - you need practice dating and you seriously need to get familiar with having sex with women, and asking out someone that you aren’t all nervous about could be a good way to get there. I mean, don’t just use them for sex, but ask one out on a casual date and see if there is any mutual interest there.
Let me refresh your memory - Every girl’s crazy about a sharp-dressed man. 
This site has some good advice for business casual attire for men. You probably don’t want to go that far since you are a more natural guy looking for a natural woman, but if you substitute a well-fitting pair of jeans or chinos for the dress pants, I think you’d look impressive on a date. You basically shouldn’t look like you rolled out of bed, threw on something from the floor, and called it good enough. Your date will likely have spent a bit of time agonizing over what to wear, and will have dolled herself up all nicely for you - it is appreciated when a guy takes the time and makes the effort to look nice, too.
My boyfriend is not a huge fan of dressing up. He doesn’t fuss over his hair and he doesn’t wear cologne. Pretty much the only time he wears a suit is for weddings and funerals. However, he does have a pair of nice jeans and a collection of button-down shirts that he puts on when we go out on a fancy date, or have to go to a family shindig. You’d be surprised at the different it makes. Not that I don’t find him attractive regardless of his attire. 
All right, I’m going to step out of the limelight now and let this thread wind down. There’s been a ton of great advice. Thank you all!
I super appreciate all the tips. I’ll report back in a few months/years/decades if things get better.
Oh, and I should add that I’ve asked a half dozen real life good friends for the same advice and not one said anything useful.
Thank you all, truly. The Dope delivers yet again.
Takesome parting advice from Courage Wolf
Don’t overthink things. It’s easier than it seems - you want to meet someone and they want to meet someone. In our society you are often on the hook to make the first move and risk rejection. That’s just the way it is so take the risk with gusto. Every one of your ancestors did and eventually succeeded or you wouldn’t be here.
Hang around the wine section at a Walmart. For some reason I always get hit on there. And I’m fugly and my clotbes all come from Goodwill, so give 'er a try.
Conversely, change your energy pattern and just decide to quit…stop even looking at women altogether. It seems it’s always when I just go on a diet when someone gets the psychic call to knock on my door with a pan of brownies.
I owe you guys a quick update.
Much to your dismay, I’m sure, I stayed Asian and vegan. After a few dates and false starts, I expanded my search boundaries (geographically speaking) on OKC. Found a girl who was a 99% match, vegan, an environmental engineer, and gorgeous and charming to boot. A few messages later, she drove 700 miles to visit my town and spent a few days here. Things moved way too quickly and we spent most of the time with each other. Then I ended up hopping in her car at the last minute and driving back to her town with her. We spent about a week straight with each other. It was a ridiculously good time for me and a pretty good week for her, I think, though she got tired of me by the end. I really, really like her and care about her, but she didn’t want a relationship, so we parted on a friends-with-benefits note. Not quite what I hoped for, but I’m grateful for the time we did share. It was a short, sweet romance.
So I suppose I learned a lot about myself and what I care about, etc., most of which was positive. And the search goes on, though it’s gonna be really hard to beat a gal like her. Regardless, I’m just happy to have had that experience – it was much nicer than I expected. I hope she’ll change her mind someday, but life will continue even if not 
Thank you all for the advice. I truly appreciate all the help, tips, and encouragement.
