The first time … calling him

woman on phoneA guy you’ve been emailing from a dating site has given you his number and requested you call if you want to talk. You’re grateful because you’re uneasy giving a stranger your phone number.

His number sits on a Post-It on your desk. You pick it up several times a day. But you put it down each time. Without dialing.

You like his profile and his pic. His emails have been interesting. So why don’t you call?

You don’t know what to say. You’re afraid of stammering and stuttering and sounding like an idiot. You have no trouble making business calls, but this is different. You don’t have much practice doing this, since the last time you dated men made the first move. The Internet, stalkers, and safety concerns have changed all that.

So the ball is in your court.

You could always wimp out and write him an email. Or an IM. Or just give him your number. But no, you want to hear his voice, and yet you’re uncomfortable giving out your number, no matter how nice and sane he’s seemed so far.

You know you need to dial the phone. But how to start?

Review his profile or whatever you know about him before dialing. If you want a cheat sheet, prepare 3 or 4 open-ended questions. Open-ended questions get people to talk more. They start with how, what, who, why, when and require more than a one- or two-word response. You could start with “Tell me about…,” “Help me understand…,” “I’m curious about…,” “Share with me…,” “I’m interested in….”

You could ask questions that elicit a “yes” or “no” answer, but then the conversation can stall. If he’s a bit nervous, he won’t elaborate. So prompt him with a question that invites him to talk more.

Also, don’t interrogate him with rapid-fire questions. Make sure you comment on his response before asking another question. And allow him to ask you some questions. I find it best to end my answers with a question back to him, even if it’s just, “What do you think on that topic?”

Here’s a sample for you.

You: Hi Mark. This is Sally, also known as SunnyBright from I wanted to call and say “Hi.”

Him: Hi Sally. It’s nice to finally hear your voice.

You: Thanks. It’s nice to hear yours, too. I liked your profile and I’ve enjoyed our email exchanges. You are an interesting guy. (A little sincere flattery is a good way to begin. Don’t comment on his pic by saying that you think he’s cute, as the pic could be from a long time ago. When you meet, he might not look much like his pic.)

(Now ask him an open ended question. Something from his profile.) I thought it was interesting that you said you were an East Coast transplant. What is the most striking difference you’ve found from living on both coasts?

(If you said, “Do you like living on the West Coast?” or “Do you miss the East Coast?” he could just answer “yes” or “no.”)

Him: The people here are more open and friendly, which is great. I haven’t had time to meet a lot of folks, but am getting some friends from work and the sailing club.

You: I remember you said in your profile you liked to sail. I love to sail, too, but haven’t been out in a long time. I love the wind on my face and being so close to the water. What’s your favorite thing about sailing?

And you’re off. On the first call, people commonly ask, “What are you looking for in a romantic partner?” But they often express that in their profile — even if it is typically nebulous. And people aren’t particularly willing to go into a deep discussion on the first call. You want to know if you might be a match, but unless he says something that is totally off-putting, you can’t really tell if you might be a match or not.

Some women also try to feel out a man’s readiness for a committed relationship and his interest in having a family. A guy may say he’s ready to settle down, but doesn’t know he isn’t until he is in a relationship. So you can ask, but a guy may say what he thinks you want to hear — not because he is purposefully lying (although some will), but because he’s not really clear on what he wants, but doesn’t realize it.

The purpose of this first call is to see how easy he is to talk to. If it is difficult to maintain a conversation, it’s not good. If he talks 90% about himself, how much money he makes (or the material goods he has that tells you how much money he makes), how horrible his ex is, or curses or gets sexual, then no need to bother meeting. However, most people are on their best behavior on the first call, so if there is nothing odious about him at this point, it’s probably worth another call or coffee.

exec woman on phoneBut let him ask! Don’t say, “Shall we get together?” or “Do you want to have coffee?” Yes, you’re an assertive, take-charge, twenty-first century woman. But this is not the time to show it. It will come out soon enough. You shouldn’t be something you’re not, but allow him to make the invitation. Unless you’re into shy men, he needs to show enough interest — and confidence — to suggest the next contact. Even if he says, “I’m up to my eyeballs in work the next few days. Let me call you back in a day or two,” that is a good sign. If you don’t want to give your number, say, “No problem. Email me a good time and I’ll call you back in a few days.”

Technorati Tags:,,,,,,,

Got a dating-after-40 topic you want Dating Goddess to address? Send your issue to


One response to “The first time … calling him”

  1. Ally Avatar

    Practical advice. Thanks!