An old flame flickers

I recently reconnected with an old girlfriend. We had not spoken, texted or seen each other in almost five years. She broke my heart about five years ago, and my mother was killed shortly after that. I’ve not dated or wanted to have a serious relationship since.

About three months ago, I told my daughter that I was ready to meet someone. So she brought up Match.com and signed me up, just so I could browse. The very first profile I saw was my exgirlfriend’s! My daughter said, “Text her, Dad. It’s a sign.” After debating it, I did. And I came to find out that she really had not dated anyone in five years, either, and that she had stopped browsing Match.com more than a year and a half ago.

Well, we started texting and then meeting for lunch and then dinner, and next thing I know, we are spending almost all our time together. I was not the best boyfriend years ago, but I changed so much after my mother’s death. And this woman really noticed a huge change in me. She even got emotional about how well I treat her and how much I spoil her and how amazingly sweet I am now. She said, “No one has ever treated me as well as you do now!” That’s exactly how I promised myself I would try to behave.

I’ve fallen in love with her. I’m so scared to tell her, and I’m so scared to lose her. But I want her to know I’ve fallen for her now much differently than I did in the past. I always ask her now, “Were you like this before — funny, smart, witty?” She says, “Yes, but you were blind to it before!” And I was. I was going through a very bad divorce and losing a business, just to name a couple of things.

How do I convince her of this? I always tell her I’m insanely crazy about her. She tells me she feels the same. We are almost 50, and I’m not sure I can go through another heartbreak. — Lost Love

Anything worthwhile comes with some risk. To win big, you have to bet big, and from the sound of this love affair so far, I’m betting on you. Just tell her you love her. Even if she doesn’t say it back, telling people you love them is great for their soul and yours.

My wife and I are in our mid-80s and don’t eat nearly so much as we did in our younger years. When we go out to eat, we usually share a meal. If we take guests out, we expect to pay for their meal. We try to allow the guests to order first, as it can make for an awkward situation if they order a full meal each and then we split a meal. I think this makes them feel uncomfortable. What is your take on this?

— W.C. in Waycross, Ga.

My take is that you’re very considerate, generous people. Based on that fact, I’m sure that however you’re handling the situation now is the correct way to do so. Insisting that your guests order first is a good tactic to ensure that they don’t downgrade their order after seeing that you two are splitting one entree. But don’t feel bashful about politely explaining, “We simply don’t have the appetites we used to, and we enjoy sharing a plate. But please, order whatever you’d like. Our treat.” Such a warm statement, said with a smile, will surely melt away any awkwardness.

I’m betting on you. Just tell her you love her. Even if she doesn’t say it back, telling people you love them is great for their soul and yours.