I am a single woman in my late 30s. I have a good job, good friends, I like my house, my family, and I get out plenty. I even go on dates occasionally, but recently none of them have caused any real sparks. I don’t feel particularly bad about that, mind you; I know that somebody will come along eventually that I can actually have a relationship with. No big deal. So I had a birthday last week. And I’m wondering, what is it about a birthday that makes exes come out of the woodwork? I am not kidding. I got text messages, Facebook messages, even an email. They ranged from guys I had gone out on a couple of dates with to longer term boyfriends, including one who was such a raging asshole to me while we were together that my friends were all relieved when he finally dumped me. I don’t get it. Why would they bother? Most of them broke up with or ceased calling me, not the other way around. What is it about birthdays?

Just Wondering

It’s called regret, JW. The guys in question are most likely seeing in retrospect that maybe they should have gone on another date/not treated you like shit. They have probably gone on to date other women who turned out not to be as cool as they had hoped, or at least, not as cool as you were. So they take the opportunity of your birthday to show you that a) They really did like you, and they want you to know that they are still thinking about you; or b) they realize that they should have been better to you, because you were actually really great and now that they have dated other, lesser women, they see the error of their ways and “look, see I’m thoughtful—I even remembered your birthday!” Sadly for them, they are too late. But perhaps by not even dignifying their pathetic attempts at re-connection, you will teach them all a valuable lesson.

My best friend in the world is a girl. She is two years younger than I am, just turned 18. We have known each other for a few years, and we hang out all the time. We talk on the phone every day, send each other texts at work and school, go out every weekend and some week nights. I have had girlfriends before, and we stayed friends. She has had boyfriends, and we have stayed friends. Now we are both single. I actually really think I am in love with her, but she has made it really clear that we are just friends, so I haven’t said anything. One time, like a year ago, after she broke up with a guy she was seeing, she said to me that she wished we could just date because it would be so much easier. I had a girlfriend at the time and I laughed it off. I assumed (and mostly I still assume) that she was just kidding.

The thing is, I really think we are perfect for each other. We already know everything about each other and our families and stuff—I mean, everything outside of sex stuff. We get along great and we tell each other everything. I am just afraid if I say anything it might screw up our friendship, and I would hate that so much. I don’t know how things would be if I lost my best friend. On the other hand, I figure she has to know that I like her, and if she wanted to actually have a relationship she would have said something by now, right? I don’t know what to do but I am about to burst. I am afraid to ruin things but I am also afraid if I don’t at least tell her, then there is no way I will know. And what if she meets another guy now and ends up with him? I am going crazy. Please help me.

You know what you have to do. Let the damn cat out of the bag and see what happens. Don’t make it a huge announcement, and if at all possible try not to put a lot of pressure on her about it. Maybe you could just ask her, on one of your many nights out together as friends, if she has ever thought about the two of you dating? Tell her you have thought about it and you would like to give it a try, if she would. I would avoid a huge, Lloyd Dobler-style proclamation of undying love, devotion, and made-for-each-otherness, because if she doesn’t share your feelings that would be a lot harder to walk back (I do hope you will excuse the political terminology, as I have been up to my eyes in politics these days). Just tell her you think you like her as more than a friend and you think you guys would make a great couple and see where it goes. You never know. She might be thinking the same thing and also wondering how to bring it up. You may get turned down, and it may hurt, but that would be better than waiting for her to get married and then finding out that you would have had a chance if only you had asked, right? Good luck.

CONFIDENTIAL TO SEXTY GIRL: Allow me to be the voice of your older self. Do not, under any circumstances, send naked pictures of yourself to anyone, or post them anywhere on the Internet. No matter how anonymous you think they are, or how much you think you can trust this guy, you never know where those pictures might land. What if he loses his phone? What if one of his less honorable friends gets ahold of it and forwards the pictures? Worse yet, what if his mom finds it and freaks out? You are young and smart and your future is full of possibilities. Do not limit those possibilities by doing something this silly now. If your boyfriend wants to see you naked, then he can do it in person. Please, please believe me when I tell you that this is a bad idea.