I would love some guidance on when and how to disclose to a man who is seemingly a very good potential match for me, that I have a serious health issue. We met online — I am 53, he is 69. During one of our early phone conversations he mentioned he was "healthy as a horse" and does not take any prescription medications whatsoever. It seemed to really be a point of pride for him. I however, am not so lucky and was unfortunately diagnosed with congestive heart failure at age 49. I have a fantastic cardiologist who literally saved my life with just the right cocktail of drugs. So far my condition is under relatively good control, hopefully for more than just the time being. If in the future the drugs begin to lose their effectiveness the only option left for me would be to be put on the waiting list as a candidate for a heart transplant.

Last week we had our first date and it went really well. We went to a beach party hosted by his country club, after which I felt comfortable enough to go back to his place with him. We had a magically hot session of spit swapping during which he not only commented what a great kisser I was, but also took my hand and put it on his very impressive erection. He then mentioned again he does not take any drugs of any kind. After an awkward moment during which I contemplated sharing my "secret," I thought better of it and instead enthusiastically said, "Wow!" We didn't end up sleeping together (my choice) and he did ask me out again for this coming weekend.

It has been so long since I've been so attracted mentally and physically to someone and we have really good chemistry. We have so much in common — we're both foodies, love live music, love to travel, etc. I felt it was too soon during the conversation before we met and on the first date to bring up my serious health issue, but in light of the fact he openly shared he had no health issues/takes no medications at all not once but twice, how and when do I tell him about my situation without it then seeming like a lie of omission?

DownRight Uncomfortable Glaring Silence

The laddie doth protest too much, methinks.

By which I mean to say: Any 69-year-old man who presses his boner into his date's hand and then offers, apropos of nothing, that Pfizer had nothing to do with it... well, that guy probably has a Pez dispenser full of Viagra in his pocket. Because why bring drugs up at all? You're on the couch, you're swapping spit, you're hard, she's into it — why bring up boner pills? Whether or not someone popped a pill is literally the least interesting thing about a boner on a 69-year-old man. Or any other man.

As for the other time he brought up drugs... it's wonderful to be in good health, of course, but there's no shame in needing an assist from a pharmaceutical company to restore or sustain good health. And this guy may not need drugs now (for boner-related or non-boner-related reasons), but odds are good he'll need drugs at some point. If he doesn't get hit by a car or felled by a heart attack — or expire from a terminal-but-natural boner — drugs are in his future. Aspirin, if nothing else, but probably more powerful stuff.

All that said, DRUGS, you didn't lie to him — not even by omission. He's not entitled to a full medical history on a first date. Let's say he started talking about his retirement savings instead of his health — that wouldn't obligate you to share your financial statements wit him. Go ahead and keep dating him, DRUGS. See if you like him, see if you like that (supposedly) drug-free boner of his, and see where this goes. You can have a convo about your medical condition if and when you get serious about each other — a medical condition that is is under control thanks to the doctor you're fortunate enough to have access to and the drugs you're fortunate enough to be able to afford.

Finally, DRUGS, he's 69 years old — this "healthy as a horse"/"drug-free boners" business could be about his own insecurity, i.e. he worries that you may think he's too old for you. He may worry that a 53-year-old woman might not want to get involved with a man who's about turn 70, lest he prove to be too old or too frail to keep up. Your eventual disclosure of your own frailty may free him to acknowledge his own.