I have been single for three years. There are plenty of reasons why, starting with needing time to get over my ex, continuing with “Hey, being single is actually kind of fun,” winding through second thoughts and an exchange of messages with said ex, then friends telling me I was stupid to even talk to him because he broke my heart. The last two years have been long and boring. People have tried to set me up. I tried Internet dating, then swore off of it, etc. I am shy and not terribly confident in social situations, to put it mildly. I love going out and I have plenty of friends but I freeze up if a guy I don’t know talks to me. I don’t intend to, and I certainly don’t want to, but I get very nervous and just lose the ability to communicate, especially if he is cute. 

The other day, I finally had a last-straw, come-to-Jesus type of experience, which resulted in me telling my best friend that I was tired and lonely and not getting any younger, and I whipped out my credit card and signed back on to the Internet dating site I had used the last time I was actually dating. So far, so good. I have had some messages and found some possibilities, and I am beginning to feel like I might actually have a date again before I die. 

Also, I got a message from my ex. He uses the site also, obviously, and it is where we met. The last two times he has contacted me have been disastrous, beginning with flirty messages and texts, followed by phone calls, “catching up” and then him not showing up when we set a date. After which, he would offer lame excuses and I would feel like shit for a month. 

So, of course, I sent him a message back (because I am dumb). Now I don’t know what to do. I know where this is going. He will want to see me in three… two… and I don’t know if I should. Part of me wonders if the simple fact that we seem to keep coming back to each other doesn’t mean something. My friends are of course freaking out and telling me to stay away from him. He did break up with me after two years in what I thought was a really great relationship because he “wasn’t ready” to settle down. What would you do?

Back in the Saddle

Well, there is obviously an attraction between the two of you. That seems clear. But it also seems like you are always at a disadvantage in the relationship. I don’t blame you for thinking about exploring the possibilities. Being single for a long time is not easy, and if you aren’t great at talking to guys, that certainly makes things harder. Maybe you can treat him as one possibility, while continuing to meet and date other guys on the site? It might be difficult—hell, it might be impossible—to casually date somebody that you had a real relationship with for two years. But if you can date him casually and continue to meet and get to know other guys, you can explore reconciliation without closing yourself off from other possibilities. 

It is entirely possible that you won’t even like him anymore, once you see who he has become. But it is also possible that whatever issues he had with lack of readiness are over and the two of you can be happy. Whatever you do, make sure you draw very clear lines for yourself. Don’t get too involved too quickly, and don’t go out with him exclusively until you know where you stand. He can’t hurt you if you don’t let him. 

So, I was at work the other day, and out of the blue I got a call from my ex. I didn’t pick it up because a) I was freaked out and b) I was at work. This is a guy who I dated for over a year, and the break up was really ugly, partially because I was too dumb to just walk away. He wasn’t very good to me, and he was not good for me, but I didn’t want to be alone. So, when he dumped me, nobody was surprised except me, and none of my friends were in any way sorry to see him go. 

The thing is, he has the capacity to be very sweet. He is a good person; he just can’t help but be a selfish know-it-all. When he isn’t like that, he can be a great boyfriend. Ugh. So, anyway, the message was basically that he was “thinking about me” and he wanted to know if I wanted to “get together and hang out.” On Valentine’s Day. What the hell? As you can tell by the timing of this letter, I missed that deadline (I had plans with friends) but now I’m trying to decide if I should call him back or not. What do you think?

Second Thoughts

I think that a guy who calls you out of the blue claiming he “just wants to hang out” on Valentine’s Day is full of shit. You don’t say how long you have been broken up, but I gather from what you said that it has at least been a few months. If he actually wanted to see you and this wasn’t just a case of his not having anything to do on the worst day of the year to be single, he had about 364 other days to choose from. In addition to being selfish and a know it all, ST, this guy is a manipulative jackass. Be glad you are clear of him. If you do happen to hear from him any time between now and the next time he might feel especially lonely (Sweetest day is in October, right?), you should continue to ignore him. Sheesh.