OK: Jewish Grandmother + Jewish mother = 100% JEW (and not no bullshit 25% Jewish - 100% straight up Jewish. Period). Don't let anyone tell you differently. You also qualify automatically for the Law of Return and the Israeli government will list you as being of Jewish nationality, free to marry any other Jew in Israel without complication. Basically the father's ethnicity or religion is irrelevant as far as the "Who is a Jew" question is concerned.

Moreover, even Haredim/Chassidim/Ultra-Orthodox Jews would agree. Maybe if you practiced another religion, the Reform movement might say you are not Jewish but since it seems you practice Judaism you can't even be disqualified on those grounds.

The main issue is dealing with your need for acceptance and approval from people you don't know well who may not care so much about you as a person(dates, near strangers, etc.). It happens to manifest itself from a Jewish perspective but it likely also manifests itself in other aspects of your life.

That being said, your issuses are not unknown amongst the Jewish people.

What I do (and I'm a convert so I SO do not have stereotypical Ashkenazi Jewish looks and have a very un-"Jewish" first and last name) is that I subtly drop "the J-bomb" by casually referring to things like Shabbat, including minyanim I daven at and Jewish events I have been to, etc. In other words, Judaism is interwoven into the fabric of my life so much that they are inseparable, and one would know I am Jewish after talking to me for a short time (especially on a 1st date).

And I am not even so religiously observant.

If you like, you could just get more involved in the Jewish community. BTW, I know plenty of Jewish men who prefer women with some T&A, including one man who loves big boobs so much that he will and has dated women as much as 30 lbs overweight just to get the pretty face and the boobs he craves. He even said to me once "I like JAPy women."

I mean, you do live in New York, the Jewish community is large and diverse enough that you can find your niche - if you want to find it.