When is Too Soon? Dating & Adoption Talk

I purposely did not date while I was undergoing fertility treatment. I just thought it would freak a guy out that I was actively trying to get pregnant. And I also didn't want to hear the bragging about how all I needed was one night with him and he'd get the job done. I heard that enough from guys I had no intention of sleeping with.

Fertility treatment is over. Most of the baby weight is off. And so I've stuck my toe back in the water.

I've met two men in recent weeks that I've had thee conversation with. I wasn't planning on having either conversation, but was completely unprepared and just blurted it out.

Situation #1

After talking a lot over the course of a week using Google chat and Skype, we finally met for lunch. I felt like we'd gotten to know each other quite well, so when he mentioned that a friend had recently adopted, I thought it was a good opening. He took it well, seemed excited for me, asked appropriate questions. A few days later, over the course of several conversations, I discovered that he was annoyed that women wouldn't date him because he has a daughter (I knew this from conversation #1) and also mentioned that he won't date women with kids. (Yea, I know...nice double standard.) After some prodding from me, he said he could not think of anything long-term with me because of the "baby" thing. OK...moving on.

Situation #2

There was very little conversation before we met for drinks. The only thing I really knew was that he was a Red Sox fan. We had a great time at the bar, playing darts. A few hours later, while watching the Yankees game, he played my necklace and asked about my St. Thomas More medal. When he asked who he was the patron saint of, I froze trying to think of a lie, but couldn't think of anything better to say than the truth. So I said, "adoption." He asked if I was adopted. Again I froze as I said no. He asked if I had or was adopting. I said yes. "Does that scare you?" (This was a mere three hours after the conversation with boy #1.) He was a trooper and took it in stride. "I just met you. You can't scare me yet."

So how soon is too soon? I know it depends on the conversations, the situation, the people involved. I'm just afraid of not mentioning it early and then suddenly it's feels like I should have had this conversation months ago. Or mentioning it too early and getting a deer in the headlights look, like "I just met you...why are you telling me this?"

Dating is hard enough. Add the fact that I've not thought about dating for the past four years, and haven't really dated anyone since I lived in Baltimore.

Oh the joys of dating. This will be quite the little adventure.

Wish me luck.