I’ve Seen Him Twice In Three Years

Chat at 1 p.m. New podcast episode here about a sports writer who paid $3,000 for a matchmaker.


I have been in an on-and-off, long-distance relationship/friendship with “Guy” for three years. It all started in 2016 when I was traveling Europe for two months. I received a message from him on a dating site, and we emailed back and forth for a day when I was in Italy. I was busy sightseeing, so I gave him my number to call me and we spoke. When I got back home, I forgot about him, then he called me out of the blue, a month after I had been back, and we spoke on the phone and texted for like three weeks. A few more weeks went by and we finally met at his house and hung out for several hours. Four more weeks go by before we hang out again. At that point, he asked me to be his girlfriend. Guy is the owner of several businesses in New York City and Florida; he is quite secretive about his life and companies. He will give me bit of information over time or if I press him.

In the past three years I have only seen him twice in person. I live in Florida and Guy lives in New York. We talk and text on the phone all the time. I did fall in love with him by talking on the phone. But like any other woman, I want in-person time with the man I fell for, so my biggest question is: “When will I see you again?” He tells me he’s trying to visit and that work is busy.

I have been getting impatient. In the past three years I have broken up with him twice due to my impatience – once over text because he just stopped calling me for a full month (that breakup lasted six months before he said he missed talking to me and asked me to be his girlfriend again), and the second time in 2017 because he broke his word about flying to Florida for the holidays.

In the past nine months I have been to New York three times for business and pleasure, however every time I let Guy know I’m coming in to town, and I give him enough notice, he said he was too busy and that he’d see me in Florida.

In the past month, Guy has been opening up more about his life and telling me he trusts me more then I know. He’s has been telling me he misses me, which I take with a grain of salt. He has been calling me more and texting and calling me in the morning before work, and ending each night with an “XOXO.”

What should I do with this Guy?

– Help


“I have broken up with him twice due to my impatience.”

You broke up with this man twice because your gut was telling you to be done with this nonsense. You’ve seen this man twice in three years. He’s secretive and dismissive, and he’s made you chase him for no good reason. You were in the same city – multiple times! – and he didn’t make a real effort to see you. This “relationship” has been all about what makes him comfortable.

I understand that there might be something seductive about being with someone who’s always just out of reach and has secrets. Maybe it’s exciting. I don’t know. But it’s much more thrilling, I think, to be in a relationship with someone who lets you in. That’s the kind of experience that involves courage. To know someone – to really see them – is the better adventure.

That’s why I must tell you to drop this man. Yes, he’s been calling and texting more, but his behavior hasn’t really changed. He’s still not in your life. He keeps asking you to be his girlfriend, but he has no intention of making you his partner. You don’t need to give him any more of your time. He’s not the Guy for you.

– Meredith

Readers? Any reason to continue this relationship?

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