The Dating Issue

Love Letters special: Dating dos and don’ts

As the author of the Globe’s popular advice column, I’ve learned the right and wrong ways to hunt for a mate.

Martin Gee/Globe staff

As the author of the Globe’s advice column Love Letters, I’ve read thousands of notes from the lovelorn, many of whom are single and on the hunt for a mate. Their situations and missteps have led me to compile these tips for navigating the dating game:

Dating Tip No. 1


Do not Google a potential mate 15 times before you meet him or her. It’s fine to do it once — just to make sure you’re not going out with a criminal — but please don’t jump down the rabbit hole. Don’t spend time on Facebook and Pinterest pages. Avoid knowing too much. It’s not just that it’s unhealthy; it also makes you a bad date. You need to be able to ask questions without already knowing the answers. There need to be mysteries to solve.

>Dating Tip No. 2



I truly believe that checks should never be split on dates. One person should always pay. If you asked for the date, demand to pay. If you didn’t ask for the date, you can offer to pay, but please don’t put up a fight — allow your date to pay for you. It’s OK. Take turns. But please, let it always feel as if it’s someone’s treat.

Dating Tip No. 3


If you’ve been on a run of blind dates and Internet-spawned outings and you find yourself exhausted, stop for a few weeks. You won’t be at your best if you’re just struggling to get through the night so you can go home and watch television. Many people write to Love Letters complaining that they keep pushing themselves to get through the next website because they’re afraid to waste time. I tell them to relax. If it’s inconvenient to be on, there’s no point forcing it.

>Dating Tip No. 4


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For the first few dates, pick casual places with low lighting. Don’t go somewhere expensive to prove a point. It’s more about atmosphere than cost. And it makes treating your partner a bit easier. This area is packed with hole-in-the-wall joints with tasty, cheap menus. Do your research.

> Dating Tip No. 5


If your dating experiences are unsuccessful or even crazy, resist the urge to react as if you’re starring in a reality show. Don’t blog about your encounters. You’re not doing this to entertain; you’re looking for a partner. Respect the experience.

>Dating Tip No. 6


This should be obvious, but it isn’t, judging from what I hear from writers to Love Letters. I get so many notes from singles who’ve gone out with people who never asked them one question. If you’re not curious about a date, something’s wrong.



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