Why did you consider converting to Christianity at various points in your life?
There were two points.
The first was early in my 20s. My mother's family, you see, isn't Jewish. They're Anglicans of British and Scandinavian stock. My mom converted to Judaism when she and my dad got engaged. And my dad's family was mostly in Montreal whereas my mom's family was in southern Ontario where we lived. So I had an upbringing where we celebrated Christian holidays alongside Jewish ones, and I went to church for various family functions on my mom's side. As a kid I thought nothing of it. Synagogue, church, it's all the same, really. A place where some old guy in a robe talks about G-d a bunch, I had to wear uncomfortable clothes to, and it's all just a preamble to food and hanging out with my cousins, really.
But as I got older and questions of identity came up, part of me felt more drawn to my mother's side of my family then my father's side, the Jewish side, simply by virtue of being around my mother's side. So I considered converting to Anglican Christianity for a bit.
The second time was in my mid 20s. And this is kind of wild. I'm gay and I didn't come out of the closet- to myself or anyone else- until I was 25. Shortly after I met a guy, and we fell in love. Like me he was freshly out of the closet and we helped each other through that. He was also a Catholic. And a devout one. Strange given that he was gay, but hey. I'm not devoutly Jewish but I do still have faith so... like... we were a couple of oddballs.
Anyway it got to the point in our relationship where it seemed like we would have to consider our future together. And for a while I considered converting to Catholicism for him. Yeah I know. I would have converted to Catholicism, a religion we couldn't even get married in. Nuts, right? But that's how I felt.
Not to get into the nitty gritty of my love life, but it didn't work out in the end.
What stopped you from converting to Christianity at each of these points?
The first one was a matter of theology. I was questioning my identity as a Jewish person, hell, as a person in general. And Anglican Christianity seemed to "fit."
But when I got serious about considering it I had to ask myself theological questions. And the big one was "is Jesus the Messiah as foretold by Jewish prophecy?" The central tenant of all Christian denominations is that yes, he is. And I worked on it, I thought about it. I considered it, and it just didn't click for me. And I decided it would be insincere of me to convert to Christianity if I couldn't believe that central tenant.
The second time? Well... I would have converted out of love. Funnily enough what my mom did. When that relationship ended up not working I was in a bit of a state, and religion was suddenly very far from my mind. When I'd gone through my requisite ugly crying and tub of ice cream I just sort of... never thought of it again.
Funnily enough I'm dating another Catholic guy now, but this hasn't come up. Probably because he's the most lapsed Catholic who's ever lapsed and I'm the most lapsed Jew who's ever lapsed
Here's the thing.
I don't hate or dislike Christianity as a faith. When I talk about Christianity's history of antisemitism I'm talking about it as a historical thing that happened, not something I hold over Christians today. When I talk about my- and other Jews- unwillingness to accept Jesus as the Messiah it's not to disrespect Christians who hold those beliefs, but just a statement of fact.
Christian history is fascinating to me- both the good and bad- and I have friends and family who are Christians. I don't have anything against the faith itself, and I admit that as a moral standard Jesus does pretty well for himself. If you actually listen to what he himself says it's a good set of lessons to live by, by and large.
Any issues I have with Christianity in the modern day is less against the religion in general and more bad actors who I feel abuse the words of Jesus, or the Bible in general (New or Old Testaments, take your pick) for political gain and to fearmonger. I don't hate Christianity or Christians though, nor do I hate Jesus.
I have a historical interest in it all, and had a theological interest at key points in my life, but at this point I'm pretty settled being a very liberal Jew.