100 lbs gone - advice required.

Just say hi. Don't buy those books that tell you to act like you're God's gift to women. Say "Hey, my name's X." Have a conversation. Ask about her interest. When she/you have to go, say "Would you like to grab coffee sometime?" I don't know any woman who would be offended by that.

Only advice I've seen that works is just get in the gym, eat right, lose the weight, get the swim suit body so to say and that does it. Assuming of course you have the other things in place, you should be ok after that. You'll have to assess yourself and be honest with yourself about your appearance.

I would have to disagree with this part... If you don't have a swimsuit body, you can still find a meaningful relationship –- as long as you don't expect her to have a swimsuit body either. A lot of big guys aren't willing to date big girls. I'm not saying that you shouldn't get healthy, but I know several couples who are both on the heavy side and are very happy together. I'm a big girl, and I've dated skinny guys, buff guys, and heavy guys. What determined the success of those relationships was not their size, but their compassion and heart.

If you're going after a woman who's a "perfect 10," yeah, you'd better work on your abs. But if you have no experience with women, you might be better served by dating someone who's a good person, but has got some extra weight too. You'd probably relate better. TL;DR: If you want to have sex with a woman with a "perfect" body, that's one thing. But if you just want to have a meaningful romantic relationship with a woman, you can do it at almost any weight.

First, congrats on your success. 100 lbs is amazing and you must feel elated to be closing in on your goal.

Now to the girl. . .

Here's the deal with MOST women (not all) we're flattered by all interest even if we don't/can't reciprocate it.

It's really hard to give specific suggestions without knowing either of you. What either of you like, what makes you laugh...
humor is the best way I've found to connect with anyone.

hmmm. brainstorming....

You could give her a humorous comic strip. Say Calvin and Hobbes or some such. Just hand it to her and say you wanted to make her smile and walk off...do that for a week or once a week for a month. Then maybe ask her out for coffee. Take your time, get to know her.

Pm me if you nee more specific guidance.

Certainly, you can say hi to this woman and see what happens but if you don't know much about her you don't know if she's even interested in dating anyone so don't place too much importance on this individual.

I spent 42 years "dating." Yup, age 12 to 54. Fat and, well, never actually thin but slightly chubby. I dated men from 5'4' to 6'7." A few years younger than me to several decades older. I tried almost every method to find someone to date from hanging out in bars and churches, hiring a dating service, flirting during singles night at a supermarket, Texas line dancing, bowling leagues, and duplicate bridge. I even did a short stint as an assistant commissioner for the boy scouts in NYC. All of these had more or less success over the years.

Now, we have internet dating sites and that has worked best of all for me and for many of my friends. With dating sites, everyone knows why you are there and they are there for the same reason -- to find a date. You get to choose, and sort, and decide in a no-harm-no-foul online environment whether you ought to meet.

Now, yes, I kissed a good many toads, and worse, in this process. I also met some nice and interesting folks where it just didn't work out. I made some friends with folks where we were suited for friendship but not dating -- and I found my Bill, the perfect person for me.

Had I not persevered, I'd still be alone. Had I given up after false starts, I'd still be alone. Was I the dumpee more than being the dumper -- yes -- at least it certainly seemed that way to me. But the game is worth the candle. There is someone out there for you. It may take awhile to find her but the adventures you will have while looking are definitely worth it.

Let's see ... there was the sporting goods store owner who took me to a little league banquet, the pot-smoking jazz musician who wrote theme music for public television, the day trader who swore he was related to the original Count Dracula (that didn't last long), the Marxist retired Madison Avenue antique dealer who introduced me to someone who had built the concrete forms for the Gugenheim, my gentleman caller from Kentucky who has called at 8 p.m. on Sunday nights ever since we dated in the 1970s, ...

Just start by smiling and saying hi. Guys have the mistaken impression that girls only want "hard bodies" of some sort.
Not true - a woman will be thrilled if you are tender, thoughtful, funny and strong. If you "feed" those qualitites in yourself they will drop like flies for you! Best of luck to you! It will happen at the right time.....