Are we just hooking up?

Dear Meredith,

I'm in my mid-20s and have never been in a serious relationship. I haven't been too tragic about my chronic singledom -- I've been mainly happy with my independence thus far, but lately, as I have been transitioning into a more stable career and social life, I've been pining for the companionship and intimacy that can only come from a committed relationship. Of course I am absolutely clueless about how to be in a long-term relationship thanks to years of living it up in the millennial hook-up culture.

A few months ago, a coworker introduced me to his best friend and we immediately hit it off. We had similar senses of humor, common interests, good conversation, physical attraction, etc. We hung out together socially as a result of our mutual-friend connection, and one night we drank a little too much and fell into bed together. With this not being my first time at the rodeo, I pretty much said sayonara to things ever getting serious with this guy due to the casual tone set by our premature drunken hook-up.

However, over the following weeks, we started spending time together and talking every day. I really felt like I was falling for him. I found him to be forthcoming with his feelings about me, which were very sweet, but he was also quite direct about how he thinks that I am a "closed-off person" (his words, not mine). In response to this, I became much more cognizant about trying to be open and forthcoming, specifically with my own feelings for him; and one night, L-words were exchange (probably prematurely, in hindsight). I had never said that to anyone before -- it was a big deal to me.

But then, and I'm not joking about this, the very next day, he started pulling away. He stopped making plans and started taking longer than usual to respond to text messages. I've experienced the male disappearing act before, so being a little sensitive, I lashed out after a week of near-radio silence demanding an explanation. His response: "I thought this was a casual thing," thus, making me feel like a delusional, crazy person. I took some time (a little over a week) to cool down and clear my head, and then decided to write him a long message about what I was looking for in a relationship and what my limits are. I didn't expect him to respond -- it was more for myself than for anything else.

A couple of weeks later he boomerang-ed on me, and like a fool, I took him back, rationalizing that he now knew what my stances were on things, so he was proceeding knowing full well that I was not down to "just hook up." Things were great for a bit, and then they weren't. I just didn't feel like he was making a real effort to be a part of my life or have me a part of his, so again, I confronted him. This time, it was less out of anger and more out of need to hash out expectations. Again, I said that I really liked him and wanted him to be a part of my life, but that I didn't get the sense that he wanted the same, so it was for the best if we went our separate ways. He agreed and said he understood where I was coming from and that he's a really independent guy and has the tendency to be wishy-washy. He went on to say that he is really cautious about getting serious with someone at this point in his life. I was sad, but I had to respect that, so I said goodbye.

I dated, I spent time with friends, I made plans, I tried to move on. But he came back ... again. And I let him ... again. When we are together, things feel perfect, so I am really conflicted. We haven't had any sort of discussion about what we are or where we're going. I'm wondering if I have been putting too much pressure on the situation and not allowing things to unfold naturally. At the same time, I also am scared that I am being played for a fool, considering I know what his stances are on relationships ... or maybe just on relationships with me for that matter. Ultimately, I'm scared that he's still living in Hookup-ville, and I've moved zip codes.

Should I try to have yet another honest discussion with him? Should I relax and just let things play out for the time being? Should I simply cut my losses at this point? Is this situation completely immature or is it indicative of the rockiness that comes when two independent, albeit naive, people try to figure out how/where to fit someone into their respective lives?

– Sick of Hooking Up, Brookline

You've already made the decision to try this again, right? It doesn't seem like you're going to cut your losses until he walks away from Round 3 (assuming he does).

My advice, as you go through Round 3, is to ask yourself whether there's any growth in the relationship. Are you getting to know each other better? Are you becoming more comfortable with him? Do you feel OK about just calling him up and making plans? Or do you walk on eggshells until he extends his own invitation?

This guy clearly doesn't know what he wants, but you've told him about your desired zip code more than once. He's either going to start meeting your expectations ... or not. You can certainly have another talk with him, but before you do, think about his actions. Is Round 3 any better than Round 2? Are you enjoying yourself?

Maybe instead of having a big State of the Union before he has answers, just tell him what you need and see if he can deliver. (And really, if he fails again, that's it. No need for Round 4.)
Readers? Should she walk no matter what? Is it possible that wishy-washy can turn into serious? Is this a millennial thing? Should she have another talk? Help.

– Meredith