Dear Workingbachur95,
After reading some of these comments above, some of which I can imagine is hurtful for you, and that I personally relate to this topic given that I am a BT who it took a while to find his match, I wanted to share with you a few of my thoughts and a balanced perspective whereas I feel others may have a hard time relating to your position.
1) Rightly or wrongly, people naturally gravitate to those who they perceive to share similarities with. For example, there is a certain well-known African American radio show host who related that in a prior stint years back as a telemarketer, he would go by a different, more “White” sounding name in order that his target market would be more comfortable to purchasing a product from him. In truth, we see this across different cultural groups, Chinese prefer to bond with other Chinese, African American with African American. The same is true to an extent in the Jewish community. A recent Pew study was released regarding marriage partners of BTs, and they found that 49% of BTs were married to another BT, 32% to FFBs, the remainder unmarried. This is more outstanding given than BTs are such a small subset of the religious Orthodox community. The irony is of course, is that each person created and brought down to this world is so different in terms of physical appearance, outlook, personal experience, etc. Now on the one hand, similarity is important. Sephardim are typically best suited with other Sephardim due to shared minhagim and culture. On the other hand, we see more often than not that when Hashem matches two people together, those two people are often so different from one another. Even if they come from the same community, one spouse might be soft in temperament whereas one might be more forthcoming. Indeed, it is often the shared differences and perspectives that helps us reach our potential.
My point here is twofold. Firstly, unfortunately it is harder for you and I to marry into a different subset of the Jewish community because of natural bias present. While you obviously can’t change (and should be proud of) your past as it has molded you into who you are today (while I assume about you the following but felt the need to state it regardless), it does help to try and “fit the bill” and try to make small changes to fit in with your target hashkafa and community. The area you live, the Shul you attend, the garments you wear, even if it is all superficial to a large extent and all that truly matters is in the heart, but it does make an impact on who you get suggested for a Shidduch.
On the other side of the coin, when you do IYH find your bashert, it should be that your differences help complement one another.
2) I found I had to accept that I was not good fit for everyone. For example, if a bookkeeper for small business is trying to sell their service to a large complex organization, it simply isn’t a good Shidduch. To be fair, some girls truly want to marry a person who is currently learning in Yeshiva. Your username “Workingbachur” seems to connote that you currently work a full-time job, and obviously I wouldn’t expect you to quit your job, but some women are currently looking for a full-time learner which currently isn’t you. I know you said you would be open to taking off time to learn for a few months, but if a girl said she wanted a guy to take off time for 1, maybe 2 years, would you consider such a thing? I know it is a highly personal question.
3) To counter the point above, virtually everyone has to find at some point a type of profession, be it within Chinuch, a lawyer, doctor, etc. So the theoretical positive is that a “hard-held Shita” that a person holds when they are 20 (For example, to marry the “perfect” Yeshiva bachur who never misses Seder, or to marry someone who is 3rd generation MO), would hopefully adjust the older they become, at 25, at 30, and onwards.
Unfortunately as we know, it is not always true. But lets say you were turned down by a woman who was 25 years old because perhaps your mother for instance, who is otherwise a lovely and kind person, may not fully cover her hair, and that would somehow affect your marriage and or future upbringing of your children (unlikely at best), and you who is a Yiras Shamayim and someone who dedicates himself to learning, do you REALLY want to spend the rest of your life with someone who may be narrow-minded. You wouldn’t be happy with that person in the first place, so thank Hashem that you were turned down from that encounter.
4) If a certain Shadchan won’t set you up with a BY girl, find one who will. While I found it was important to be appreciative of Shadchans as it is a truly thankless job, even if they couldn’t suggest anyone for me, at the end of the day it is part of our hishtadlus to try and find the right one for us! Don’t discard other avenues for finding the right person for yourself – whether it be online (might not attract Yeshivish, but certainly some wonderful people available) or singles events / Shabbatons, where you are judged on your own merits from the outset before someone looks at a piece of paper, it is certainly part of our Avodah to put our name out there.
5) As a side note, I think it is utter nonsense to suggest that if you have made a conscious decision to become more Yeshivish, that you might come to drift away in the future. As you are someone who made a change in his life, which I can imagine had its own challenges associated with it, and has stuck through with it, I can assume your worldview is grounded from the combination of life experience and personal growth.
6) Lets face it, we have a natural tendency to want to label ourselves and to categorize different types of people, MO, Yeshivish, etc. Our mind naturally categorizes and compartmentalizes different thoughts and ideas. For example, when we see a buffet of lunch menu items before us, we categorize the items into solids and liquids, American style dishes and Chinese food, etc.
Of course it is inappropriate to label people, when we are so diverse in thought and action, but we do it anyways. The reality is that you can’t really avoid the categorization as someone who comes from a left-wing MO family, but at the end of the day, even though you’ll have to work harder than others to marry the right one for you, but point #7 rings true.
7) At the end of the day, we always have to remember Hashem is in control. All we can do, is become the person that we wish to marry, to actively work on our middos, improve in our learning, etc. in order that we can be zocheh for the right person for us. While at the end of the day, unfortunately it is simply more difficult to move towards dating BY women due to cultural differences, perhaps a more insular nature to the community, finding a good Shadchan for you, but if that is what Hashem wants for you, then at that time there is nothing that will stop Hashem from sending her to you if you become the person you are supposed to be.
Wishing you a wonderful shavua, and IYH you should be sent the right person at the right time and at that time you will know the wait was worth it.