Once again, as they do every year, my thoughts turn to dating when you’re in the 2nd Chapter of your life.  Last year, a good friend shared this blog entry written by a man about to marry a widow and his thoughts are really encouraging:  https://onefitwidow.com/marrying-a-widow/

Many women who’ve lost their spouses hope that they will eventually marry again.  To get there, it typically requires you to get out there and start dating again.  Regardless of your age, I think you’ll find that it’s different dating the 2nd time around.  We have to do it with an open mind, a willing heart and a sense of adventure!  The dating stories that I hear each year at the Dallas Chapter meeting always bring tears and smiles!  There’s that inevitable excitement that comes from finding someone else to whom you’re attracted, the sadness that comes from the first time your vulnerable heart gets broken again, and the amazing “wow” that comes from actually meeting someone else to whom you can give your heart again.

One of the most common questions that comes up when re-entering the dating world is “Who should pay?”  If the average age of widowhood is mid-fifties, many women are re-entering the dating scene at a point where they are as financially secure as the men with whom they are going out.  So who should pay for the dates? Let’s assume that if he’s asking you out for that first date, he’s going to pay.  But what about thereafter?  When should you offer to start helping out with the entertainment costs?  And if you ever take the lead and ask someone out, would you pay?

Today I spoke with a woman who told me she wants to keep enough flexibility in her financial plan to prepare for the fact that she may eventually remarry someone who doesn’t have her same financial means.  She based this on the fact that she had been dating and no one is as financially secure as she is.  She was okay with that fact, although I have also spoken with plenty of women who felt that they wanted to meet a man with similar financial means or more financial means.  I’ve met women who wanted to pay from the very beginning so that they retained a sense of freedom and independence.  Other women were willing to pay after the relationship reached a certain level of commitment and others felt that until they were remarried, he should pay for everything.  What are your thoughts and can you share stories of how this as worked or not worked for you so far?

I’d love to hear your thoughts about paying for dates in this 2nd chapter of your life.  Send your thoughts and comments to: joy@modernwidowsclub.com