Dear Rabbi, I went to modern orthodox schools as a child and teenager, but now associate with the Yeshivish hashkafah. On dates, the boy might ask me why I went to those schools and if I still associate with them. for shidduch purposes, am I allowed to say that I dont associate with those hashkafos anymore and that I never really fit into those schools? Thanks
The issue is complex because truth is an ideal, but also marrying a ben-Torah is, as well. Although there is room to tell an untruth for the sake of other important ideals (if you read Hebrew, please see http://asif.co.il/download/2%20(21).pdf where I elaborated on the topic), usually honesty is truly not only the best, but also the most beneficial policy. The best way to get from one point to another is via a "straight" line! Especially regarding he who may be your future & eternal soul-mate, you should be totally open and honest for the truth inevitably gets out (e.g. when you are with your parents and husband together) and then you look bad, and seem like a liar. Also, he should know, accept and love you for who you really are. Nevertheless, if there is a certain fact which is clearly counter-productive and may prevent you from advancing an even more important ideal, where for example, such knowledge by a certain person may automatically "disqualify" you (sometimes even before you meet!), then you can not tell the truth for that purpose.