Life Advice



Ask Anna: Can you start a relationship long distance? Plus, breaking up with kindness

Anna Pulley, Tribune News Service on

Published in Dating Advice

Dear Anna,

Two months back, I (39F) instantly meshed with a man (36) at a concert. Despite the seven-hour distance between us and a mutual disinterest in romance, daily texts and weekly marathon calls quickly became our norm. He affectionately called me “babe” and his texts were often flirtatious. I told him I wanted a long-term commitment. He said he wanted the same. However, his upcoming travels delayed our meeting.

I admit, doubts started to creep in about his lifestyle choices and communication style, since I seemed much more invested in regular communication. He reassured me, yet prioritized his social life over us talking. I’m supposed to go visit him for a four-day weekend in a few weeks and as our meeting nears, our texts have cooled, prompting mixed advice from friends on whether to pursue this or walk away.

Feeling the crossroads of compatibility and the fear of fizzling, I'm wondering if I should cancel our impending rendezvous or see if in-person chemistry might rekindle our initial spark. Any advice is sorely appreciated. — Crossroads Conundrum

Dear CC,

My initial response is that if you’re already feeling those twinges of disappointment and lifestyle red-flaggery — and your relationship has barely begun! — it’s probably best to listen to them.


Plus, you’ve got seven hours of distance between you, which is hard even in existing committed relationships, but for new ones that don’t yet have their trust, intimacy and communication skills built up, it can be a death knell right out of the gate.

That said, spending a little time with him in person might be the antidote you need to get clarity on your feelings and to determine if you’re actually compatible. Then again, it might just confuse things further — especially if you spend the four-day weekend in a haze of sex, which … who wouldn’t?

However, you don’t need to make any decisions right this second. You can be a little uncertain for a while. You can feel it out. Whatever you decide, keep a healthy dose of skepticism about you. Enjoy your time together, of course, whether that’s virtual or in-person, but keep an eye on those feelings of unease or uncertainty that come up. And most importantly, listen to them before they become screams.

If you do meet, use the long weekend to ask some of the harder getting-to-know-you questions: on topics like marriage and kids (if that’s important to you), conflict (as in, how do they handle it), what their values/priorities are in life, what a healthy relationship looks like to them, thoughts on monogamy and so on. Intersperse this with the weekendlong sex haze and you’ll be on your way to at least getting to know them a little bit better!


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