I like my late friend’s husband

I'm a long-time lurker, first-time writer. I'm in my late 30s, never married, never been in a long-term relationship. While I've long hoped to find a spouse and raise a family, I have also been determined not to wait for a relationship to start "living" my life. I have a great job, which I enjoy, and which provides a reasonable standard of living for me. I have had many opportunities to travel, both for work and for pleasure. I come from a strong family and have fabulous nieces and nephews with whom I love spending time. I've always been pretty independent and self-sufficient but would love to find someone to share my life.

I have a dear friend, "Andy," whom I've known for about 15 years. He's 20+ years older than I am -- a widower with teenage children. I was quite close to his wife before she passed away a couple of years ago. I've gotten to know him well over the years and we've become much closer since his wife passed away. As strange as it may seem given our age differences, I find myself more and more attracted to him. Between work and being a single parent, he's very busy, and we don't see each other often. When we do, it's just a straightforward social setting, often with the kids. We talk on the phone frequently, sometimes multiple times a day. He hasn't shown any interest in pursuing another relationship since his beloved wife passed away. I'm loath to do anything that might jeopardize our sweet friendship, but I would love to explore the possibility of a relationship with him. I've been hoping that with time he would come to see the potential I see in our friendship - but I don't think he's looking for another relationship (yet?).

I'm a fairly patient woman, and can continue to wait, if necessary, but I'm trying to find a sensitive way to explore the possibility of a relationship. Can you offer any suggestions on how to approach the situation? Should I simply let it play its course?

– Puzzled and Hopeful, Massachusetts

PAH, patience isn't always a virtue. You shouldn't be sitting around and waiting for him for years -- unless you're sure that there's something to wait for. My advice is to ask him what he thinks of your relationship and what it all means. Try the honest truth: "Sometimes I wonder if this is going somewhere beyond friendship. Do you? Because I'm confused, puzzled, and hopeful."

But please, before you do that, spend some time thinking about what you really want. Are you interested in him because you're really falling for him or because he's safe? Are you up to raising kids -- and are you comfortable dating someone significantly older? Has your friendship with this man -- specifically the phone calls -- given you an excuse not to seek out men your own age? Is this a real intimacy or is this about staying close to your friend who passed away?

I'm not trying to lead you anywhere with those questions. I'm just curious. And I don't want you starting something up with this man if you're not up for those big things.
Think about what you want. And if it's really him, have a discussion. Because while you're waiting patiently for him to make a move, he might be waiting for you. Or maybe he thinks of you as a daughter or a niece. If he's not going to date you, you need to start setting boundaries in your head. Pronto.

Readers? Should she bring this up to him? Does this relationship have potential? He calls her a lot -- but doesn't see her much. What gives? Discuss.

– Meredith