Is it okay to ask a man out on a second date?

by singlemomseeking on January 15, 2009

This post is for the folks who are tired of hearing about The Bachelor, you know who you are!

One month after posting “The man I hope to love,” I put myself back online. I was ready to date again.

Or, so I thought — until I went on a few bad dates and wanted to hide again.

Then, I got this email from a guy who’d emailed me when I was previously on JDate, in 2007. We’d had a string of emails back and forth, and then shared an awkward email moment: both of us confessed that we’d just begun dating other people and were going off JDate.

My gut, however, told me that he was a good guy. So, I sent him my direct email. (He didn’t write back, which he explains below.)

“There you are again,” he wrote to me recently. “I found our messages from a while ago. I have to say, your last message was very sweet, and I did consider writing you offline, but we had both starting seeing others, and so I declined…. Anyway, would you be interested in a chat?”

This time, I sent my phone number to him.

He called during the day, which can be an awkward time for a first conversation. But it was spunky, fun, and smart. Some of you also know that I’m a sucker for a deep voice.

What was the problem, then?

I didn’t know what he looked like! Sure, he had a few photos online — but he was wearing sunglasses in two of the photos, and looking down in the third. What was up with that?

He emailed me the next day to ask me out for dinner and a play. That was against my “first date rule” — only short coffee dates for the first meeting — but I promptly broke that rule.

“You’re so cute!” was first thing I said when I saw him. He’s intellectual-looking, with glasses and a goatee.

I wanted to know: “Why are you wearing sunglasses in all your photos?”

“But I like those photos!” he said.

Within two minutes, we were having our first fight. But it was a sweet, affectionate fight.

Our first date was filled with fun, insightful conversation. The night ended with a brief hug on the street corner — and the quickest peck on the lips.

During the date, I’d told him that we’d just celebrated my sister’s birthday that afternoon. He’d asked why I hadn’t brought him a piece cake.

The next morning, there was an email from him:

“Rachel, You’re quite something. I had a wonderful time with you tonight.”

I was bringing him some cake that afternoon for sure! (I hear some of you now: “Slow down, Rachel!”)

I emailed him about the cake. He wrote back:

“Rachel, if you ever want to see me again, you bring the cake.”

(His sense of humor is very similar to mine, extremely dry.)

Then he gave me his home address.

I told him, “You’re giving me your address, you don’t even know my last name! What if I’m a crazy lady?”

Do you know what he said?

“You’re a mom.”


I left the cake on his doorstep (he wasn’t home), and he emailed to thank me.

But here’s the deal: he hasn’t asked me out on a second date.

Four days have passed since our first date. No more emails, no phone calls.

Now what? You know that I encourage women to ask a man out.

I want to! But unfortunately, my assertiveness has scared men away in the past. I’ve come on too strong, too fast. I’m afraid my boldness might mess this up.

Should I ask him out on a second date?

What should I do? Or, not do?

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