Marrying someone with a similar background makes for better understanding and an easier adjustment.
A person who’s looking to marry someone who lived a more restrictive or pristine lifestyle should expect that they’re likely to experience more resistance in the shidduch market.
Marrying someone from a more sheltered background happens all the time. I think the issue is that you need to be prepared for some rejections and understand why they are coming (and you can choose to ignore them and keep on moving forward). When it comes to shidduchim, people are very wary, and if they have a choice to be meshadech their daughter with someone who’s never veered off the path, you might have a harder time getting in through the front door.
That’s why connections are very important. People who are respected in the community will recommend you, and the respect and trust that they earned will translate into greater trust in you and giving you a chance.
Can I ask you a question, though?
Why would you reject anyone who had the same background?