Ask Natalie by Natalie Bencivenga

Time to Rekindle Old Romance?

DEAR NATALIE: I've been talking to a woman I went to high school with, about 20 years ago. I had a HUGE crush on her back then. She still looks amazing. Her husband died four years ago and she has two teenage children. I really want to ask her out. However, I don't feel I'm attractive enough for a woman like her. How can I put my self-doubts aside and just go for it? -- FEELING LOW

DEAR FEELING LOW: Sometimes, we can get so caught up in our own heads about something that we never act on anything and life just passes us by. What do you have to lose by asking her out? Nothing. And what do you have to gain? Possibly a new relationship, or if nothing else, a fun night out. Life is too short to wish for things and never pursue them. Many people don't follow their dreams because they are afraid of succeeding. Many don't believe they are worthy or good enough for what they want. How sad is that? We are all entitled to support our inner dreamer, and if pursuing her brings you joy, then go for it. Remember this: You have no idea how she feels about herself, either. You may think she is beautiful, but she may not see it. So assuming that you aren't good enough is all relative. Tell her how lovely she is, and watch her face light up like a Christmas tree! 

Natalie's Networking Tip of the Week: Feeling the daggers on you? Networking isn't all sunshine and roses. Sometimes people don't want you in social inner circles because they are threatened by your A game. But all of that is just background noise. Kill people with kindness, and watch the ones who are out to steal your shine slowly fade away. 

Please send your relationship and lifestyle questions to or tweet them to @NBSeen. You can also send postal letters to Natalie Bencivenga, 358 North Shore Drive, Pittsburgh, PA 15212

(This column was originally published by the Pittsburgh Post-Gazette.)