Advice to shadchanim: When you ask a single what she/he is looking for and she/he responds, don’t assume that you know better than them and have the right to give them mussar and tell them that they are wrong for thinking that Type A is more likely to work for them than Type B.
You have some preconceived notions about the reasons why people are single and you are making the (incorrect) assumption that if an older single girl tells you that a guy in klei kodesh is more likely to be “matim” for her, don’t assume that she must be wrong and that it must be that she is too picky, and that she has been refusing to date guys who weren’t in klei kodesh all these years and that must be why she is still single, and that it is your job to convince her that she has to marry a working guy.
Most of the time you don’t know her, or if you do know her, you don’t know her that well. Chances are that you don’t know her entire dating history, who she has gone out with and why, and why it hasn’t worked. You have no idea why she is still single.
As a matter of fact, the chances are that she knows herself better than you, and probably has a good reason for what she is looking for. After all, she has a lot of dating experience, and she probably spent a lot of time thinking about why her dates didn’t work out, and what she should be looking for.
Don’t make assumptions, and don’t be so haughty as to assume that you know better than her/him and that you have the right to tell him/her that she is wrong. The fact that you mean well doesn’t mean that you are right, or that you are not causing a lot of damage with your words.
Maybe the issue is not that she was only dating learning boys, but that she was only dating working boys, and now she realizes that’s not “matim” for her. Don’t make any assumptions, and please don’t assume you know better than the singles themselves.
