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Dear Annie: I’m 22, working full time in the city, and recently started dating a guy I met through a mutual friend. We’ve only been seeing each other for about a month, and he really is a sweetheart. The problem is, the more I get to know him, the more I wonder whether we are simply in very different places in life.
He is in his late 20s, lives at home and works part time as a delivery driver while waiting to start a city job sometime next year. I understand that people go through transitional periods, but from what I gather, he was unemployed for about a year before taking this job. He also has a college degree but decided he doesn’t want to work in the field he studied.
I’m trying not to judge him, but this is very hard for me to understand. I’ve worked since I was 14 and have had a full-time job since I was 20. My career is stressful and, frankly, I don’t even love it anymore, but I’ve always been someone who worries about the future and feels pressure to keep moving forward.
He seems to feel none of that urgency. When I gently asked whether he might want to work full time while waiting for the city job, he simply said he was doing fine.
That difference between us is starting to show up in other ways, too. He can be immature, and while I initially found his carefree personality charming, I’m beginning to wonder whether what I saw as easygoing is actually a lack of direction.
Then things got complicated.
A few nights ago, we were meeting his friends at a bar when he asked me to be his girlfriend in the parking lot. He had apparently already told all of his friends he was planning to ask, and they were waiting inside. I felt completely put on the spot and panicked, so I said yes.
Now I suddenly have a boyfriend, and I’m realizing I may have preferred this relationship when it was casual. I enjoyed spending time with him when there was no expectation of a future attached to it. That feels unfair to him because he is a genuinely good person and deserves someone who is excited to be with him.
I also know I’m not blameless. My own anxiety about work and success probably isn’t the healthiest measuring stick for everyone else. And I should have been more honest before things reached this point instead of avoiding an uncomfortable conversation.
But now that I’ve said yes, how do I tell a kind person that I don’t think we are compatible without making him feel as though I’m judging his job, his living situation or where he is in life? -- Already Having Second Thoughts
Dear Having Second Thoughts: You are not breaking up with him because he is a delivery driver or lives at home. You are considering ending things because the two of you seem to have very different ideas about ambition, adulthood and the future.
That matters.
And saying yes because his friends were waiting inside was understandable, but a parking lot proposal is not a lifetime contract. Be kind, be clear and do it soon. Tell him you think he is a good person, but you don’t feel the two of you are the right match.
At 22, dating is partly about discovering what you want and, just as importantly, what you don’t. Better an awkward conversation now than months of pretending later.
“Out of Bounds: Estrangement, Boundaries and the Search for Forgiveness” is out now! Annie Lane’s third anthology is for anyone who has lived with anger, estrangement or the deep ache of being wronged -- because forgiveness isn’t for them. It’s for you. Visit http://www.creatorspublishing.com for more information. Follow Annie Lane on Instagram at @dearannieofficial. Send your questions for Annie Lane to dearannie@creators.com. COPYRIGHT 2026 CREATORS.COM