Life doesn’t come with convenient signposts letting us know which is the path to happiness and which is the path to misery, so we’re stuck taking blind gambles. Sometimes we choose well. Sometimes we don’t. Sometimes we have chances to change mistaken choices we’ve made. Sometimes we don’t.

But all along the way, we’re guessing and hoping, no matter how much thinking and reasoning we bring to bear on our choices. And we frequently end up with regrets that we carry to our graves.

I thought about this Saturday because of a woman I met and talked with. She’s consumed with trying to make a decision that will affect the rest of her life. Although the specifics of her story are very different from what happened to me, the feelings she described were enough to remind me of where I was four years ago this month.

We’re going to call her Ashley. She has two men who want to marry her, but she can’t decide what to do. She’s dated both of them, but the relationships have been very different. With one guy, she feels the magical connection that most of us want to feel and that a few of us have felt in a very real way. But that relationship had problems. It had great highs, but great lows. She saw things in him that she knew needed work — for both of them.

The other guy is completely different. There aren’t the highs and lows, but there also isn’t the magical connection. What’s more, she feels that he needs her far more than she needs him. He’s apparently a great guy who will be a good father and husband — and he’s more financially stable — but the things she likes about him are mostly in her head, not her heart. He needs her — and wants her — so much that she feels guilty.

The first guy is about to move to the other side of the country. So while she’s been waffling about who to choose — and felt she had plenty of time to keep waffling — she feels that she’s run out of time. She has to decide now — and she’s scared of making the wrong choice.

As Ashley told me her story, I flashed back to July of 2008. I’ve mentioned a bit of this story before, but I’m going to tell you a very intense part that I’ve never had reason to tell before.

In my own way, I was torn between two women. I was in love with the one I was dating at the time, but I was scared of some things I saw in her (and things I saw in myself, too, even if I wasn’t honest enough with myself at the time to see it that way). There was another woman who I’d had a very odd relationship with before I let myself meet and date the first woman. The second woman was something of a “project.” Her life had been a mess when I met her, and I had invested a tremendous amount of time in “rescuing” her.

In the spring and early summer of 2008, the first woman and I had talked a lot of marriage. I had some legitimate fears about things in her that I didn’t understand at the time, but I knew I loved her and wanted her. She was very much in love with me, and she wanted to marry me. By early July, I had decided that was what I was going to do. I took a weekend to think about it to be sure. I realized that marrying her was what I wanted. All that was left was breaking the news to the other woman — who had been hoping all along that I’d end up with her.

On Saturday, July 5, 2008, I arranged to meet the second woman at a restaurant to talk, so I could break the news. I knew she was going to be hurt, but I had no idea what the night was going to be like.

I felt terrible telling her that I was going to marry someone else. Because of the way I was raised, I have a very difficult time not giving other people what they want, emotionally, even when it’s not right for me. So I felt guilty. Even though I knew I loved the first woman, I felt that I must be doing something wrong.

What’s worse is that she begged me to change my mind. She told me about how she had grown so much since she had known me and that she was afraid of what would happen to her without me. We started talking at about 7 p.m. and we were still talking when the place closed at 11. We moved to stand in the parking lot near our cars for another hour or two. Then we moved to the parking lot of a nearby convenience store.

She begged me to change my mind. She cried. I felt awful. I tried to explain why I needed to marry the other woman — that I loved her and that we were more compatible — but it was gut-wrenching. I told her that it was what I wanted and needed to do — and that’s the way we left it when we finally parted around 4 a.m.

As I drove home, I felt drained and miserable. I didn’t know what to do. I knew who I loved, but I couldn’t bear hurting the other woman as I was. And the more I thought about that, the more I found excuses to justify delaying a decision. I waffled back and forth. To make a long story short, early in the week, I made one of the worst decisions of my life. I told the woman I loved that I couldn’t marry her. I was refusing to make a definitive decision.

For the next six months, I talked to both of them. The one I loved begged me to marry her, and I knew it was what I wanted. I just couldn’t get the emotional courage to make the definite choice. (I did finally buy an engagement ring for her, which I still have.) I talked to the other one, too. She was hoping the first woman would be out of the picture and she could finally have me. I felt guilty, loving one but not wanting to hurt the other.

Almost seven months after that fateful night in early July, the decision was taken out of my hands. The woman I loved gave up on me and moved on. It destroyed me in ways that I will never be able to explain to anyone. The only positive outcome is that it forced me to get really serious with myself and work hard with a good therapist to figure out the reasons why I’d done some of the things I’d done. But I’ll never get over it.

Even though I’d lost my “true love,” the other woman was still there and waiting. I eventually started seeing her regularly, but there was never any real feeling or connection there, despite the fact that I tried to force it. I couldn’t commit to her, because she was a convenient, pragmatic back-up plan, not a woman I loved. Eventually, she realized that I was never going to love her and she realized that I was always going to love the other woman, so my back-up plan walked out of my life later that year.

I had two choices of really wonderful women. I was in love with one of them. The other one could have been a good and stable wife, even if I could have never had the connection I had with the first. But I lost them both — simply because I wasn’t willing to make the tough choice that I had to make.

When I talked with Ashley Saturday, I gave her two pieces of advice.

First, I said, do what your heart says. If you’re sure you love one of them, choose him over the other one, even if the other choice is more stable and seems like more of a “sure thing.” There’s a reason that most of our songs in life are about intense love, lost love and being desperate for real emotional connection. There’s also a reason that we don’t write many songs about which husband can build you the bigger house. As you go through life, it’s the emotional connection and understanding that count. Call me crazy, but I think that’s what matters.

Second, I told her, make a choice. I told her the story that I’ve just told you, and I told her that the worst thing she can do is to keep trying to sit on a fence between them. Even if she can’t see how it’s going to happen, trying to have it both ways was going to mean she would end up losing both choices. I told her which choice made sense to me — based on what she was saying — but I told her whether she agreed or not, she had to make a choice. And she had to trust her gut.

I have no idea what choice Ashley will make. We had a long and intense conversation Saturday afternoon, but I might never hear from her again. (I gave her my card and asked her to let me know what she did.) After she walked away, all I was left with was to ponder my own history — and my own devastating loss.

I watched the love I wanted and needed get washed away because of my indecision. I pray Ashley chooses better than I did, because failing to choose leaves a person with regrets that will remain until his or her dying day.