Ok I seem to be the only female single here.
Yes, it’s very uncomfortable to be asked by pretty random people, pretty personal information, such as your age. When in Shidduchim, you don’t have the option of telling someone to get lost, as you don’t want to be viewed as difficult or rude, so you generally find yourself in a position of being asked all sorts of questions with almost no gracious way out of having to answer.
Some tips for those kind, well meaning people, looking to help a single find his/her bashert (thank you for trying to help!!):
Make sure the setting is appropriate (if you’re not sure whether the person is comfortable discussing personal topics at that time/place, ask for their number and if it would be ok to call to discuss an idea you have). Obviously, if you do ask for their number, you MUST follow up!!! I hope I don’t need to explain this one!
If/when you do feel that you must know certain things, preface it with, ‘I hope you don’t mind my asking’ OR ‘I understand if you don’t want to divulge this info, but do you mind my asking…’ OR ‘who can I speak to about …’.
With regard to age: No, do not be so direct- instead, show some sensitivity and ask ‘within what age range do you usually date’ of both sides, that will give you the answer. (If the guy will for example only date girls younger than age X and you are unsure whether the girl is X+1, X or X-1, you can tell the girl that guy will only date girls who are X or younger and she can let you know if she feels that she is appropriate.) You do not really need to know the exact age, just within what range to look or consider candidates for this person. It’s really not your business. Leave singles their dignity and don’t invade their privacy by asking questions that you don’t really need to know the answer to.
To some of you, not familiar with the level of pain and anxiety that (female?) singles function under on a constant basis, this might seem strange and over done, but trust me- most singles (esp the females) are self-conscious about their age). And as we are at the mercy of society to set us up, we are not in the position to tell people that their questions are intrusive and inappropriate. So please, have some sensitivity and at the very least preface your questions with, ‘I hope you don’t mind me asking…’.
(FYI: Yes we do mind you asking, but we appreciate you acknowledging the intrusion, and thus preserving some of our dignity by your attempt to be sensitive).
It’s always better to be oversensitive to the feelings of others, than to be insensitive and risk hurting people who are already hurting so much inside.
I also agree with Poppa: If you have a professional relationship with the single, have someone else make the suggestion. As a single, there is nothing more awkward than having someone with whom you have a professional relationship with (ie. the mother of a student or client) set you up, or/and be the in between person etc only to have it not work out in some unpleasant way, and to then have to continue your professional relationship with them. Trust me. Been there done that. Really awkward.