I did not expect to have to write this post so soon. I’m just shy of a month in my new role, with my new employer, in my new city, and I didn’t really expect dating to be part of the equation just yet. Well, not exactly.

This past Sunday night, I was chatting on the phone with a friend who isn’t really a friend (you know those guys, the ones who aren’t quite comfortable with the friendzone but for whatever reason, or maybe for many reasons, you haven’t dated). We were talking about dating in my city and at some point I mentioned that I had declined a date. Despite what I felt were legitimate reasons for not going on a date with an almost adolescent (seriously, he was 25 and looked 18) my friend accused me of “avoiding” or being “hesitant” to date, despite my expressed interest in finding a partner that could lead to something long term. I don’t know if it was the nature of our relationship, how he said it, or the accuracy of it all, but it got under my skin a bit. That night, I took a decent photo of myself (I am not particularly photogenic) and signed up for an online dating site.

On Monday, encouraged by the response to my mostly blank profile, I added a couple more photos, completed the “about me,” and the “essay.” Later that evening, I got a message from someone to whom I will refer to as “Lawyerman.” Lawyerman had a really interesting profile so I responded. After exchanging several e-mails and text messages, we decided to speak on the phone. In addition to having a nice phone voice, Lawyerman is smart, funny, articulate, direct, open, and we stayed on the phone for far too long. Before the end of our conversation, he asked me out on a date for Friday evening. Despite my shock at the speed with which everything had happened, I happily agreed.

So here I am, dating again. And while there are immediate challenges to dating while paying off debt (affordable dates) there are also some long term challenges. Like, if the person you’re dating is in a better financial position than you are (perhaps as a result of being older, in a more lucrative profession, or just making smarter financial decisions), when, and under what circumstances do you disclose your more meager financial position? When you’re planning your first trip together? Cohabiting? Engagement?

I think there is a chance my friend-not-a-friend was correct but perhaps just not for the reasons he suspected. I think I attach a great deal of shame to my debt (past financial mistakes) and I think the idea of having to share that information with anyone feels like…exposure. For now, I am just going to focus on having fun on my date with Lawyerman (I suggested we go bowling) and leave the tough stuff for another day.