Should I go for Mr. Safety, or wait for Mr. Married?

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Dear Prudie,
I met a guy about four months ago and we hit it off wonderfully. I like everything about him (so far) except for the fact that he is still married. Separated, for sure (I checked with mutual friends), but I consider that still married and not available and told him when he's free we could pursue a relationship. No guarantees that either of us would be available then, considering the length of time divorce takes in California (at least six months) and that divorce papers were just recently filed. (Again I checked; it's public info!) We do not see each other but do e-mail now and then, mostly just saying, "Hi, I'm thinking of you" kind of things. In the meantime, I have met another guy who is great, definitely single, and is crazy about me. And I should be crazy about him, except he's not guy No. 1. I know that if I had never met guy No. 1, I would be more interested and excited about guy No. 2. Since I won't compromise on the separated/married thing, do I wait five months and see what happens when, or even if, guy No. 1 is free? Or do I get him out of my head, somehow, and give guy No. 2 a fighting chance? I know this sounds so darn high school, but we are all mid- to late 40s.

—Bakersfield, Calif.

Dear Bake,
Prudie admires your scruples and suggests you make a "fate bet." Because you wisely choose not to dally with a guy who could be married for quite a while—for whatever reason—why don't you proceed with No. 2 as if there were no No. 1? See where things go. If he is not your heart's desire when/if No. 1 sheds the Mrs., you will have given yourself every advantage in making up your mind. This has nothing to do with the "bird in the hand" thing ... it is merely a rational way to play out your situation. And who knows? It is entirely possible that a Mr. Perfect No. 3 could wander into the picture. Good luck.

—Prudie, alternatively  

Dear Prudence,
How does one encourage safe sex without promoting promiscuity? I have a younger sister in her late teens who I suspect is sexually active. I have come to the conclusion that the only person in our immediate family she is going to get straight facts from is me. From experience, I know that any such talk from my parents would be of the Bible-thumping variety and extremely judgmental. How do I convey a message of safe sexual practices without coming across as first, a busybody, and second, encouraging what some might term a "liberal sexual agenda"?

—Older Brother  

Dear Old,
Given that your parents would not be a fount of purely disinterested medical information, you are exactly the right one to have a talk with your sister about the birds and bees ... who, unfortunately, these days, bring with them many sexually transmitted diseases. Correct information can in no way be construed as "encouraging" sex. It is neither liberal nor conservative to wish to avoid AIDS, herpes, genital warts, numerous other venereal diseases ... or an unwanted baby. Because you have a hunch your younger sister is already sexually active, you would be doing her a great favor by allowing her to be comprehensively informed.

—Prudie, proactively 

Dear Prudie,
My best friend (I will call her Anna) and I are 39. We have been through absolutely everything together, from our unfaithful husbands, subsequent divorces, my second divorce, and my pregnancies. Anna, after many disastrous relationships (mostly because she displayed her desperation to get married and have a baby), has married a man our age who is equally desperate to have a baby. Three days ago she found out that her eggs are too old and she will be unable to conceive but is eligible for IVF with a donor egg. Anna was previously on anti-depressants but no longer is, as she was trying to get pregnant. She has spent three days locked up in her house, calling in sick to work, and not communicating with her husband. When we "talk," I simply listen and keep asking what her husband feels about what she is saying, because this is a crucial time for them as a couple. I love her so much and can see and hear the pain, but I cannot empathize as I had my two children in the last six years and feel happy even though their father traded me in for his second "fling." I need some resources or canned answers to gently show her that she is fortunate enough to be able to carry a baby if she chooses (a few of our other friends can't) and that her husband would accept adoption—though Anna hasn't decided about adoption. She isn't getting any younger. Her 40^th birthday is next week, and I fear her depression will peak on that day. Help!

—Stuck in a Cluster of Infertile Friends