Question: Does Judaism have anything to say about a woman pursuing a man? I dated a guy twice, he likes me but is undecided because of the long distance situation and I wonder if it’s a lack of respect for a woman to pursue the man?
Answer: While there might be subtle details of your particular relationship and background that could affect your choice, I would suggest that, in general, you are not obligated to act entirely passively in your relationships.
Tamar, you will remember, was rather proactive with Yehuda (Braishis 38) - although I would definitely not carry that analogy too far! Avigail, it could be argued, was quite aggressive in her early relationship with David I Shmuel 2).
On the other hand, being too forceful might not be appreciated. Perhaps you could search for relatively indirect ways of communicating with this young man (sending neutral regards through mutual friends, the odd email with some interesting link that you think might interest him, etc). Let him know that you’re still there and interested and hope that everything else falls into place.
I wish you (both) all the best!
With my best regards,
Rabbi Boruch Clinton