Ask Natalie by Natalie Bencivenga

Should you sign a prenup the second time around? Friend owed you money and caused relationship to end?

DEAR NATALIE: I am a 40-something whose first marriage ended in divorce. I have three children with my ex-wife. After the divorce, I just about left everything to my ex — house and everything in it — so that my children’s lives would remain as normal as possible. Since then, my ex packed up and moved out of state. It has taken me close to eight years to rebuild my life, especially since I pay a healthy child support. I finally own a house again and have been able to put a little money back on my 401K. I’m finally not living paycheck to paycheck. I also met a wonderful woman over two years ago who I adore, and we are engaged. I have never been someone to care for someone else’s stuff and have worked hard for what I have, but I have a dilemma. My fiancée doesn't have much, but she has saved up some money for buying a new house. We live in my current home, but she still wants to move to a different town and buy a house together. We don't plan to have any children together. Having gone through a divorce and losing a lot, I admit that I am afraid of losing everything again. Am I out of line to ask for a prenuptial agreement? 

We briefly talked about it once before we got engaged, but the conversation needs to happen again soon and I am not sure how to bring it up. I also want her to know that I am not interested in what she has and would like for her to feel that whatever she brings into the marriage, she keeps in case of a split. I adore and love her. I know that the fear comes from my past and that I am not getting any younger. If I have any chance to ever retire, I can't take any step backward financially. We are a great couple together and I don't want to give her the wrong impression.-- MR. TORN

DEAR MR. TORN: You shouldn’t feel guilty or bad about wanting to protect your financial future. You have been through it and it is understandable that you’re nervous. Approach the topic gently — it seems as though she is already aware of your past financial struggles, and communication is key.  Yes, love is the most powerful force in the world, I believe that to be true. Yes, it can overcome anything. But, that doesn’t mean you have to lose your head when you are in love. Be honest and say to her what you wrote to me. This isn’t about your relationship uncertainty; this is about learning from the past. Sit down together with a mediator and hash out what you could both live with should the marriage not work out as planned. Think about your prenup as relationship insurance and nothing more. Hopefully, you will never need it, but if you do, at least you put something in place while you were both in love and kind to one another.

DEAR NATALIE:  I had a bad falling out with a good friend a few years ago. We haven’t spoken since. It was over money, but looking back, it was really petty. She owed me a few hundred dollars and it turned into a passive aggressive situation. We stopped talking and I never got the money. She wasn’t on social media for a long time, but I recently noticed she was back on Instagram. Part of me wants to reach out, but the other part feels like she was the one in the wrong and she should apologize to me. What do you think? I miss her and I would like to reconnect. I don’t expect to be paid back but I’m willing to let it go if she acknowledges it. -- MONEY PROBLEMS

DEAR MONEY PROBLEMS: Money and friends don’t mix well. It’s always a good idea to keep this in mind when loaning money to a friend: 1) Can I afford to lose this money? 2) I’ll treat this as a gift to them. If they pay me back, wonderful. If they don’t, I won’t set myself up to become angry and resentful. 3) If you can’t commit to one and two, don’t loan anyone money. Period. I’m sure it did become awkward over time, expecting her to repay you and then never getting any money back. Maybe she forgot, maybe she couldn’t pay it back and felt embarrassed, maybe she misunderstood the situation. Whatever the case, I’m sorry it led to the demise of your friendship. Now that you are in a different place, can you move forward and put this in the past? How important to you is that apology? I wouldn’t reach out unless you are certain you can move on from this, because it’s clear you’re still not over it. I don’t blame you. From your perspective, it’s hard to have respect for someone that you see as perhaps ungrateful or unaware of how she treated you. Maybe she will apologize and you can both move forward. There’s only one way to find out. Go for it and see where the chips fall.

Natalie's Networking Tip of the Week: Follow through with your words. If you commit to an event, go. If you promise to call and set up a meeting, do it. People will judge you by your actions and will reciprocate based on their own experience firsthand.

Please send your questions to Natalie Bencivenga to her email,; or through postal mail to Natalie Bencivenga, 358 North Shore Dr., Pittsburgh, PA 15212. Follow her on Twitter at @NBSeen and on Instagram @NatalieBenci

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