More than friends?

I met "Jake" two years ago when a mutual friend introduced us. Instant attraction, but I was dating someone. We ran into each other several times over the next few months and my friends were in shock about how much chemistry we had. I called him out on it two years ago through an email and he replied that while I was attractive, we clicked better as friends. Since I was dating someone at the time I took it with a grain of salt.

Fast forward two years later and we are friends, we text daily, talk on the phone several times a week, he meets me out for drinks, and we talk about how hard it is being single. People still comment on our chemistry but he has not asked me out or implied that he wants more and seems happy when I meet a new guy. (He does hound me with questions about the new guy and gives advice or says, "Don't date him he sounds like a tool.") I compliment him all the time but he rarely returns the compliments.

Since I already asked him about his feelings for me two years ago and was shot down, I don't want to ask again, nor do I want to ruin our friendship. He has hooked up with random girls over the past year but nothing serious. I want more but am afraid of ruining our friendship. Maybe "he just isn't that into me," but really, what guy texts a girl countless times a day if he doesn't like her?

– Just a Friend?, Mass.

There are many men (and women) who text platonic friends countless times a day. Texting is the easiest way to get a pat on the back. It's instant validation. It doesn't have to mean much.

My advice is to talk to Jake about his feelings again. It's been two years and it's time for an update.

If he says that he still doesn't see you as girlfriend material, you should rethink how much time you spend with him and whether you want to continue with all of the texts. I understand that you don't want to lose a friend, but no matter what happens, this relationship has to evolve. Jake must become a romantic partner or turn into a real, platonic, I-forgot-to-call-him-back-because-I-was-too-busy-with-my-boyfriend buddy. This is purgatory, and it isn't fun.

Tell him how you feel and what you want. Ask him specific questions about what he wants from you. If you don't have the talk, you could wind up thinking about this for another two years. There are better ways to use that time.

Readers? Is Jake just scared because she's dating other people? Would he give her this much attention if he wasn't interested? What's holding him back? Should she bring this up again? Help.

– Meredith