Dear Meredith, I'm a late 30s, never-been-married guy. Over the last decade-plus, I have become extremely close with someone we'll call Sally. When Sally and I first met, I told her on more than one occasion that I had an interest in dating her, only to be shot down. At a holiday party this past season, we got drunk and ended up going home together. This was not something I ever envisioned happening between us, and I did not know how to feel about it. And we never ended up speaking about it. A few weeks ago we ended up kissing again, and that was followed by a long conversation about the entire thing. She admitted that she is completely attracted to me, and also that she loves kissing me. However, since our lives have become so intertwined, she insists that we can never date because she is afraid. She will not, however, tell me what she is afraid of. She told me she knows that it will hurt at times, for both of us. I'm smitten ... no, I'm in love with her -- and knowing us as well as I do, I am positive that we can make ANYTHING work, as long as we communicate about it and remain 100% honest with one another. How do I go about convincing her that we can overcome anything while not seeming as if I am harping on this issue? Or should I just move on and take the hurt if/when it comes?
– Dazed and Confused for So Long It's Not True
I'm sorry, DACFSLINT. Sally is a confusing lady. My advice is to set boundaries. Big ones. I assume that Sally is afraid of making this relationship complicated, but it already is. There's no going back. She can't have you as a friend. And that's what you have to tell her, that you can't walk around pretending that you're happy with the way things are. If she's serious about being friends and nothing more, all you can do is minimize your contact with her to get over her. My hope is that when you set these boundaries she'll either a) realize that she's got nothing to lose and commence making out with you or b) disclose whatever it is that's holding her back, assuming that it's something that goes beyond the normal fear of loss. You want to keep things 100 percent honest. Sadly, that means dating her or separating yourself from this situation until you can look at her without being overcome by longing. You're not harping if you bring it up again. Just be honest about what you'll have to do for yourself if she can't reciprocate your feelings. You can't let this go on for another decade. Readers? What's up with Sally (who is not our Sally)? Is there hope here? Is his age relevant to what he should put up with? What specific boundaries should he set? Discuss.