Our families were raised together

Meredith,

For the sake of anonymity, let's call him X. Our grandparents were best friends back in the day, and pretty much raised our families together. Last year, my family flew out for an event of his family’s. X and I spent the night talking and drinking. We laughed a ton, and I found him to be far more interesting and charming than the teenager I had remembered him as. I found myself trying to sit next to X and being fully engulfed in everything he had to say. The next night, our younger generation went for drinks downtown. Though there were about 15 of us, X and I were inseparable, and even ended up dancing together at one of the bars. That night, he kissed me for what seemed like hours. It was electric. We stayed up talking together until about 4 a.m. before finally saying goodnight. I flew home that morning.

After that, we kept in touch for a few months through FaceTime and texting. We live on opposite coasts of the US. About three months into that, I found myself flying to his coast for another family event. X drove hours to see me while I was there. We played it off as though he was there to support my family, but X and I knew the reality. We were only able to steal a few minutes alone to talk in his car, and he kissed me again. After that, he offered to fly me out to see him, and I was over the moon. I am still in college, and he's six years older and has a job that keeps him very busy. We have drifted in and out of contact over the months since I saw him, and I started to think the novelty of a hidden affair may have worn off for X. His offer of flying me out to see him hasn't happened yet.

Fast forward two months since that trip, and I left for the summer on a research job out of the country. I don’t have signal down here to text him, so I haven't had a way to contact him since I left. I am completely hung up on him and have thought about him about every day since I have been here. I think I may be in love with him. I’m scared that when I return to the states next week, it will be too late; he may have moved on over the summer or forgotten about me. I hadn't exactly been up front about how I feel about him either. In fact, I was quite coy over the months before I left. I was scared to get too attached. I worry that he thinks I'm the one who moved on. What should I do when I get home? Do I reach out, or wait for him to? It’s so complicated, and the last thing I want to do is make things awkward or painful between us. Our families will be doing Christmas together this year too, which could be a good or bad thing depending on how this goes.

– Lovesick & Overthinking


First, return from your trip. It's possible you've been consumed by thoughts of nightclubs and kissing because you've been so isolated this summer. Give yourself the chance to get back to your routine. Then see how you feel.

If this man is still on your mind, it'll be time to get some answers. Once you're home, you can reach out and tell him what's up. You don't win much by keeping secrets or playing games. This person is going to be in your life no matter what, which means you need some clarity about his intentions.

When you talk to him about your feelings, you can let him know you're not expecting final answers or some big plan that involves a betrothal. You don’t know who will be living where, and you're not asking for guarantees that you're the one for him. All you want to know is whether he believes there's potential, and what he thinks might happen during Christmas. You're thinking a lot about Christmas, and a possible visit to his coast. Is he?

Basically, has this been as meaningful to him, and if so, does he have any idea what he wants to do about it?

It’ll be a conversation to help you frame this in your brain. Ask him for help with that – and stay honest.

– Meredith

Readers? Drop this now? Ask for more?