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Don’t ask older singles what they are doing about shidduchim unless you have a specific shidduch in mind or know of a particular shadchan with whom you are PERSONALLY familiar. Telling someone that he he has to get serious about it or that there are shadchanim listed in the phonebook is not only embarrassing, but it is an insult to the single’s intelligence. Also, don’t ask singles where they eat on Shabbos unless you intend to invite them for a specific meal. I’ve been in that situation before and I found it very uncomfortable.
As a single, I find it very uncomfortable when people ask “what are you doing about shidduchim?” At 35, it hurts enough. Then when I ask them if the person if he/she knows of anyone, they say I should talk to a shadchan. Thanks. But I beleive I could have figured that out by myself. So my advice is don’t mention the issue unless you are able to do something constructive about it.