Dating for Dummies: How to Write a Captivating First Message

Anthony Faccenda

In this week’s installment of Dating for Dummies, we’ll tackle two major questions facing most online daters: how long should you talk to someone before you meet and what exactly should you say in a first message. Although they may appear to be rudimentary queries, knowing how to answer them will mean a world of difference.

I have been talking to this guy from a dating site for about 2 weeks; we have exchanged phone numbers and text at least once a day. He seems like a great guy, and we communicate well, but he wants to meet, and I am nervous. How long should we wait to meet? Will he grow impatient and move on?

Sarah (27) - Lincoln, RI


Hi Sarah,

The answer to your question is quite simple. You should meet him right away, and yes, he will grow impatient and move on if you do not meet shortly. Honestly, I could gauge whether I wanted to meet someone after one or two messages on a dating site. I personally preferred meeting in person prior to texting, because you start to run the risk of exhausting conversation topics. Not to mention, texting and speaking face-to-face are two vastly different things. You won’t know if you and he click until you meet.

I also firmly believe that men and women start to idolatrize each other the longer they communicate virtually before meeting in person. Inevitably, you begin to build a false image of the other individual and it soon becomes too much for him or her to live up to when you meet. Additionally, excessively talking through text or online prior to meeting removes a lot of the spontaneity from the first date.

As for whether he will grow impatient and move on: of course he will. I don’t know how long it’s been since he first mentioned wanting to meet up, but the longer you prolong it, the more he’ll think you’re avoiding him and don’t want to meet.

I’m not sure what website you two met on, but there are plenty of other women on there whom he can also communicate with (or may already be communicating with). Two weeks in the online dating world is eons longer than in the real world. During these two weeks, other women may have messaged him or he might have messaged other women.

So I say, just meet up already. It’s totally normal to be nervous about meeting, but wouldn’t it be a lot less nerve-racking if you just meet him already? What have you go to lose? Also, bear in mind that he’s probably just as nervous to meet you.

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I never know what to say in my initial message to girls on OkCupid. Should I just start off with a simple, “Hi, my name is…” or should I get cutesy and clever?

-Jason (31) – Fall River, MA


Jason,

A woman I briefly dated, whom I met on OkCupid, once told me that she received approximately 75 messages per day. Out of curiosity, I asked her what made my initial message stand out. She went on to explain that far too many guys send generic messages, which a woman can spot from a million miles away. Believe it or not, many men (and some women) will send the same exact message to everyone.

Examples of this are: “Hey, I enjoyed reading your profile and think we have a lot in common. It’d be nice if you’d like to meet up sometime.” Although this message seems perfectly harmless, it will not get you noticed. It’s extremely trite and possesses zero originality.

As for the woman I mentioned earlier, according to her, what stood out most about my message was that I mentioned a specific point from her profile and asked her a question about it. Specifically, she had mentioned a band in her profile, so I asked her if she had seen them perform the last time they’d come to town. Luckily, she had attended the concert, as had I, so this led to instant conversation.

Women want to be able to discern that you read their profile and the best way to illustrate this is to cite a fact or commonality in their profile and ask them about it. It’s the easiest way to start a dialogue and it shows that unlike the vast majority of men on the site, you actually read what they wrote.

Be forewarned; don’t ask too many questions in your opening message. You’re not quizzing her; you’re just trying to strike up a conversation. Also, be brief. A few well-crafted sentences, three to five tops, is best. Anything less appears lazy and insincere, while anything longer can be overwhelming.

In regard to whether you should get “cutesy and clever,” I say emphatically no. Doing so will likely result in you coming off as either a creep or a weirdo. Keep in mind, this woman has no idea what your sense of humor is like, so messages like that can easily be misinterpreted and likely deleted. This should go without saying, but never use Internet-speak or comment on a woman's photos in your first or any message. And remember, spell check is your friend. 


Do you have an online dating inquiry? Simply send an email to [email protected] and I’ll answer your question in the following week’s article.

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