Dating Dilemmas: When He Shows Interest, But Not Action

By: Jenn |


Every week I share advice and stories and tips from my dating arsenal, gleaned largely from personal experience and the shared experiences of my close friends. At 25, I feel I have a substantial (though not exhaustive) dating repertoire, and it’s been a while since a dating situation has stumped me.

But now I’m stuck, and I’m reaching out to the We Love Dates community for advice!

Here’s the situation: I met a guy at a bar a few weeks before the holidays. He was there with his brother, and my friend had to leave before I finished my drink so I stuck around and chatted with these two. Though he was admittedly a little tipsy, he was cute and super flirtatious, so when he grabbed my phone to call himself so he would have my number, I was more than a little bit into it.

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He proceeded with the now-standard follow-up text the next morning, and after a few days of sporadic texts, he finally got around to asking me out.

For coffee.

Before work. 

I politely declined a 6 am date, but suggested something after work would be better. We continued to text a few times a week, but no concrete plans were made. The holidays are a busy time, and I’m sympathetic to the demands on people’s time because I have the same holiday obligations to see friends and attend parties and tie up loose ends at work before the new year.

But after a few weeks of constant “We should get together!” messages and no action, I wrote him off as not interested and moved on.

Until a few days before Christmas, when I got a text apologizing for his radio silence and showing interest in going out after the holidays. Since then, he has checked in every few days and claims he is committed to grabbing a drink soon.

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Here’s my dilemma: is this behavior indicative of a flaky personality? Is he even interested in me? Does the hustle and bustle of the holidays warrant a free pass, or should I be skeptical? 

Any advice YOU have for ME this week would be great!