Q. I am dating someone whose first name is the same as my son’s middle name. Is that even a shayla? Or is it just a matter of kibbud av v’eim not to marry someone with the same name as your parent’s names? Does it matter if the parent is no longer alive?

A. Since as is it is only your sons middle name, the complete name is already different.
The above are only minhagim and traditions that in case of need can be overridden by adding an additional name.

See question 3493 regarding a bride that the name of the mother of the proposed chosson, is the same as hers.

We wrote: The tradition of both the groom and the bride not sharing the names of the counterpart parents, is based on the Tzava’ah or last will and testament of Rav Yehuda HaChasid, written in the beginning of Sefer Chassidim.

On question 175 in regard to shunning a marriage to a woman whose father’s name is the same as his we wrote that
“this is to be found in the Will (letter 23), where he adds; “And if he did marry her, he should change name, maybe there is hope”. Some retrace the above to the Arizal (Mizmor Leasaf p.110).

A number of reasons are given: Firstly, Ein Horah (evil eye, Chidah ‘Bris Olam 447’ Heishiv Moishe 69, Chazon Ish, Maase Ish 215 ). Some maintain that it will cause an infringement in the respect due to the father, as his daughter will call her husband by his name in front of him. (Yad Shoul Y.D. 240 ‘ Mevakshei Torah 24 p.155).
Horav Shlomo Miller’s Shlit’a opinion is that there is no concern if the names are not exactly the same.”

Some Poskim maintain that the Tzava’ah applies only to his family and descendants (Noda Beyehuda E.H. 2: 79). However, others maintain that it refers to all. Therefore, usually people are indeed careful.

Divrei Chaim (E.H. 1: 8) mentions that in his circles, they specially avoid marriage when the name of the bride is the same as her future mother in law. A similar opinion is to be found in Tzemach Tzedek (Y.D. 116) quoting the Baal Hatanya. However, he permits changing the name in a minor way, as do others.

Indeed there are Poskim that also maintain that if the mother in law is usually named by a given title, such as Rebetzin, there is no concern. (Tirosh Veitzhor 214).

Horav Shlomo Miller’s Shlit’a opinion is that for those who maintain that tradition, indeed they can be lenient.

Rabbi A. Bartfeld as revised by, Horav Dovid Pam, Horav Aharon Miller, Horav Chanoch Ehrentreu and Horav Kalman Ochs Shlit’a