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The struggle to communicate with potential dates in text messages is real

How do I make a connection with someone else in texts?

Love Letters

Globe Magazine.

Q. I’m a 28-year-old guy who has moderate success getting phone numbers, but sometimes I struggle to get to the first date. I’m a history major and serious writer and have a hard time coping with the limited nature of text messaging.

How do I express genuine intimacy and enthusiasm over a text message?

– Limited

A. One of my first jobs in the Features/Arts section of the Globe was writing about things to do in Boston. The column wasn’t just a list of events; it was also supposed to be a fun read. The challenge was that I only had about 75 words to describe each event. I couldn’t ramble on. The work taught me that crafting something short can involve more “serious writer” skills than a 5,000-word story.


It surprised me then, but now it’s obvious. Social media has shown that some of the best writers say plenty with a small number of characters. Short messages are not limiting; they are a great challenge.

Texts can communicate great intimacy and enthusiasm. The text of your letter is 55 words — one of our shortest ever — but I get a strong sense of your personality, goals, and frustration. You are capable of being clear and concise, with emotion.

My first piece of advice is to be honest with people when you’ve hit a wall with texts. Say, “Hey, up for a call? My brain is done with texting for the night.” A lot of people will be thrilled to escape the back and forth. After you get to know someone a bit, you can tell them that texting is not your favorite way to communicate.

My second piece of advice is to text questions. Whenever you’re stumped, make it about the other person. So many people monologue about themselves. Show that you can be curious.


A third piece of advice: Read some Dorothy Parker. She always reminds me that you only need a few words to say the most important things — with great spirit.

– Meredith


Even the most serious writers have moments of levity and self-deprecating humor. . . .Texting isn’t much different than flirting. LUPELOVE

If you’re getting numbers, you obviously do a decent job with chatting in person. You can use texting simply to set up a date and not get into big discussions beforehand. Or you could just say up front, “Hey, I’m not great with texting, so how about e-mail or talking on the phone?” DANGLEPARTICIPLE

What exactly are you trying to convey between getting a number and setting up a first date? The communication should be simple and task-based, such as, “When and where would you like to meet for coffee?” There shouldn’t be any expectation of intimacy, and reaching out and planning is enough enthusiasm at this point. SETTINGTHEWORLDONFIRE

I bet you will find a partner who enjoys your long texts. Just don’t write them while driving! I, for one, love getting interesting texts. They are thought-provoking and show the person cares enough to spend a few minutes writing it. The only thing is, it may take your partner longer to get back to you if they need to wait until a good time to sit and read it. LITTLEPENGUIN456

Find the new season of the Love Letters podcast at loveletters.show. Send your relationship quandaries and questions to loveletters@globe.com. Columns and responses are edited and reprinted from boston.com/loveletters.


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