Effort is Everything: Initiating Conversation That Leads to Connection

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Men, I’m going to let you in on a little dating secret. In today’s world of 24-hour everything, 280 characters, constant distractions and abundance of availability, the thing that will ensure you the most success in dating is...effort.

And by effort, I don’t mean wining and dining. I don’t mean whisking her off to romantic destinations and spending tons of money. All of that is great and there’s a time and a place for grand gestures, but in the age of online dating, a little effort — especially in the beginning — means everything.

Here’s how little you need to do to show a woman you’ve met online that you value her and ensure you get a date in real life (which is kind of the point, right?!).

Initial email and/or texts:

ASK HER QUESTIONS.

Nothing is more frustrating to a woman than a one-sided conversation. I promise that you aren’t infringing on her if you ask her what she does, where she’s from or what she likes to do for fun. Don’t be that guy who answers with one word if she asks you a question or worse, answers and doesn’t ask anything back. It’s called Conversation. That means it’s 2-sided. Take an interest.

And of course, it goes without saying that questions need to always be appropriate and based on how long you know her. If you haven’t met yet, no innuendo unless she’s opened the door. And even then, you might want to let it lie.

Here’s a sample of what not to do:

Her: Hey John, your dog looks adorable. What is his/her name?

You: Thanks. Her name is Lola.

Her (now waiting for you to ask her something, but if you don’t she might try one or two more times): Oh cute name. So, what do you do for fun?

You: Workout, surf, play music. Usual stuff.

Her (now likely annoyed but giving you one more chance): I’d love to surf. Maybe you can teach me one day?

You: Sure.

And there goes any chance for your date. I guarantee it ends there. But here’s how that conversation could go with a little effort:

Her: Hey John, your dog looks adorable. What is his/her name?

You: Thanks, Stephanie. Her name is Lola. She’s a rescue. Do you have a dog?

Her: Oh cute name. I don’t have one but I love dogs and I grew up with a German Shepard. So, what do you do for fun?

You: Workout, surf, play music. Usual stuff. What about you?

Her: I kickbox, love the theater and am a trivia junkie. I’d love to learn to surf. Maybe you can teach me one day?

You: I’d love to! But how about a coffee or a drink first? When are you free? 

Her: Sounds great. How about Wednesday?

Three little questions made all the difference in her being indifferent and you getting a date. And the best part is she feels valued. She feels like you want to get to know her (which you do) and you can hold your own in a conversation (this is HUGE for women!). No one wants to go out with a dud or a self-absorbed you-know-what.

So how do you continue to show effort moving forward?

Stay tuned for my next post on easy date planning, logistical consideration and how to get a second date.