I have never wished I'd found Judaism earlier for reasons of dating or marriage. But one occasion did make me regret converting at the ripe old age of 32: When rockets were raining down on Israel in late 2012, I contacted an organization that coordinates volunteer IDF service for American Jews. I was years past the cut-off age for women, but I was convinced I could make my case to be the exception to the rule, especially at such a dire time. Trust me, I know this is somewhat laughable. I pretty much left the womb in heels and makeup. Staying in a cabin with my family in the fall and showering with well water is my version of roughing it. But I am strong. A big part of this is thanks to my mom, from whom I learned a very "can-do" approach after my parents divorced. I also believe that every person has a deep "in case of emergency" reservoir of strength they can draw from when they need to.
So while I knew I was an unlikely candidate, I had to try. I couldn't stand to do nothing, not after everything Judaism had given me. I'm aware that I will probably (and unfortunately) see many more such conflicts in my beloved Holy Land in my lifetime, but since this particular one was the first I'd experienced since deciding to convert--and just months after my JDay--the pain, guilt, and helplessness I was feeling was brand new.
This isn't Charedi-bashing. I know and know of far too many amazing Ultra-Orthodox Jews to make any sweeping negative generalizations. Rather, it is very difficult for me to understand just why they would refuse to defend our beautiful country, as so many righteous Jews have done before. Beyond these feelings, though, I have to admit I'm a bit out of my depth on the topic, so I leave it to a knowledgeable Rabbi to make a very compelling argument (as shared by my Rabbi on his blog).
Shalom al Yisrael.