Ladies: Get Your Match to Ask You Out!

One of the biggest complaints I hear from women is that they’re frustrated with engaging in long email exchanges with matches who never seem to get around to asking them out. These women have dutifully answered at least a half dozen thoughtful questions inquiring about their past relationships, favorite hobbies, and professional motivations. Yet instead of reading “It would be fun to grab a drink some time,” they get this: “So, tell me more about why you like hot yoga.”

What’s an exhausted pen pal to do? You don’t want to cut him loose just yet. After all, you’ve invested so much energy into a lengthy correspondence that it’s only natural to force yourself to keep going in anticipation of the reward at the end. On the other hand, these emails are time-consuming, and you risk slowly getting annoyed when your match asks for the third week in a row if you have any fun plans for the weekend. That’s because he’s clearly not making any fun weekend plans with you. Irritation isn’t a great way to start a new romance.

That’s especially the case if you’re suspicious about why it’s taking forever to even broach the topic of moving the conversation into the real world. After weeks of chitchat, you can’t help but wonder: Is he just stringing me along while he’s dating someone else?

The point of pre-date correspondence is to pique someone’s curiosity with a thoughtful profile and get to know each other a little better through guided communication and a few e-mails. The key is a “little” better. You still want to meet as soon as possible to see if there’s a real-world connection. (Three email exchanges is a good number.) What’s the crime in waiting too long? Besides feeling frustrated, you lose enthusiasm. By the eighth email, you’re tempted to respond with something short and sweet, such as: “Yes, I had a great weekend. Visited my parents and went to a friend’s birthday party. What about you?” Now you’re in the danger zone for the Big Fizzle.

Should you just ask him out? It’s a confusing question, especially when we’re adhering to traditional gender roles these days. (Read “First Dates: Who Should Pay … And Why” to understand why it’s a good idea in early dating.) In fact, 90 percent of communication on eHarmony is initiated by men, according to the company’s data crunchers. It would make sense that women might be cautious about disrupting this dynamic by taking the lead. And let’s face it: It just feels better when a man is really excited about meeting you.

Yet it can’t hurt to give someone the benefit of the doubt. Perhaps your match is shy or scared of rejection and is just using emailing as a stalling tactic. That’s why I’m proposing a third way. You don’t have to ask him outright, and you don’t have to feel resigned thinking about how you’re going to answer his 10th email inquiring about your relationships with your siblings.

Here are a few suggestions on mastering the art of the nudge:

1) Be curious

If your match writes about a big topic, such as why he decided to change careers or move from Miami to Seattle, you can offer a subtle hint with: “I’d love to learn more. Sounds like that deserves a longer conversation someday.”

2) Be playful

If your match asks you a question that requires a long response, such as “What’s on your bucket list?” you can respond, “That’s a great question! But I’m gonna need a cocktail to answer that one.”

3) Be appreciative

You can assume his inaction is out of respect for you and try writing: “I enjoy how we’ve gotten to know each other through our epic emails, and I’d feel comfortable taking our conversation offline.”

The key is to stay positive. You never want to put your match on the defensive by asking: “Are we ever going to meet someday?” You also don’t want to sound critical of his approach by writing “I’m not really into endless emailing.”

There’s always a chance your match still won’t get the hint – or worse, graduate to endless texting. Perhaps he’s ambivalent about meeting you. Or he’s busy and waiting for his schedule to open up before suggesting meeting. Or there’s someone else.

Whatever the case, you have nothing to lose – except the 20 minutes it would have taken you to answer another long email.

What tactics have you used to move along your match?

About the Author:

Sarah Elizabeth Richards is a journalist and the author of Motherhood, Rescheduled: The New Frontier of Egg Freezing and the Women Who Tried It. Her writing has appeared in The New York Times, The Wall Street Journal, Marie Claire, Elle, Cosmopolitan, Slate and Salon.

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