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Predicament of the Week
In which Breakup Girl addresses the situation that has, this week, brought her the most (a) amusement, (b) relief that it is happening to someone else, and/or (c) proof that she could not possibly be making this stuff up.

Dear Breakup Girl,

Here's my tale about an Internet-based love (well, dating) triangle. In March, I met a cool woman (Woman #1) through "Internet Dating Site #1." We went out on three dates, plus went out with a group of friends on three or four other occasions. After the second date, I was still getting closed body language from her, yet we continued to have great conversations in person, on the phone, and via e-mail. I figured she'd just want to be friends. Sometime after the second date, I brought my friend ("Friend") along to an event that Woman #1 was also attending. They hit it off and became friends immediately. A week later, after our third date, Woman #1 gave me the ol' "Let's just be friends" routine, which I agreed to, because I still liked her as a person. Three days later, Friend asked me if it was cool to ask Woman #1 out [kudos to him]. Because of her nonverbal reactions to me before she'd even met Friend, I knew that he hadn't "taken her away from me," so I could deal with it.

Fast forward: they had a two-month relationship, the first month filled with great times, laughter, and lots of sex (I got a lot of innuendo from both of them... barf). The second month was hellish, as they really got on each other's nerves, and Yours Truly was in the middle. The breakup was so bad that Woman #1 initially didn't want to be friends with me if I was still friends with Friend. However, I'm a pretty good amateur counselor myself, and I calmed her down in a quick four hours or so(!).

IN THE MEANTIME, I had moved on with my dating life. I found Internet Dating Site #2 and had gone out on dates with several women from there. No one who lit up my life, but at least I had something better to do on Friday/Saturday night than hold up the bar with my buddies like usual. (Oh, yeah, it may help to know that we're in Sillycon Valley, the land of the surplus single straight males.) Friend, once he'd shaken off the effects of the breakup (took him about 10 days, he was way less affected by it), decided to try out Site #2 for himself, since I'd been meeting women through it with some regularity.

And yes, as any seventh-grader who knows what foreshadowing is, we very shortly ended up contacting and getting dates with the same woman. (This really isn't that surprising, as she was a new member, and us wolves generally leap right onto the fresh meat.) I contacted her first, last Wednesday, met for drinks on Thursday, and did pizza, a movie, and drinks on Friday. When I dropped her off, I got a nice little good-bye kiss--nothing heavy duty, but with a lot of promise, if that makes sense. The following day--Saturday afternoon--I'm chatting with Friend about the weekend, and when I described my date the night before, he replied that he'd just had lunch with her! We compared notes, and it was indeed the same person. Since I'd kissed her, and because I think he felt guilty about what happened with Woman #1, he called her and told her about the situation, and bowed out. Or at least, he tried to.

Woman #2 and I played phone tag for the rest of that weekend, but we finally caught up with each other Monday night. I had realized that, in all honesty, it wasn't up to us guys; it was up to her. However, I was pretty confident, 'cause of what Friend had already said to her (I know what he said because of the context of her v-mail messages to me when we were playing phone-tag), and hey, I'd already kissed her, so she was at least attracted to me.

Well, I was wrong. When we spoke Monday night, she "...was very sorry to do this to you [me], but I feel that I have more in common with [Friend]. If you guys weren't friends, I'd be dating both of you, but..." she [correctly] thought that it would be too weird, considering.

NOW, at long last, this is what I need your advice on. I told Woman #2 that I was very disappointed, because we got along so well--as she agreed--BUT I would stand aside, and be friends with her. HOWEVER, in so many words, I told her that if [when] it didn't work out, I would want to go out with her then.

BG, I normally feel like I can't go out with a woman after a good friend has gone out with her (past "that certain point," of course). In this situation, however, I just really, REALLY like Woman #2. AND, being the referee at the trainwreck of Woman #1 and Friend, I know that Friend's personality and temperament are going to be issues with Woman #2. Of course, I can't tell her that, because what kind of jerk would I be if I knifed my buddy in the back like that? Certainly not one worthy of going out with Woman #2! (To my horror, I started going down that path, anyway, but quickly retreated.)

SO, BG, by telling Woman #2 I would wait for her, did I do the right thing, or did I just label myself a doormat? We have e-mailed each other in just a friendly, chatty type fashion, so we're definitely being friends, or friendly. My Dark Side (tm) wants to ask for advice on ways how to let her know why Woman #1 and Friend didn't work out, but I know that's evil. Part of my anguish here MAY BE the fact that I "lost." Here I am, with my good friend, and the woman picks him over me. This ain't too good for my ego, needless to say.

After Friend starting dating Woman #1, I swore (to him, her and Everyone) that I would now keep my dates away from my friends until I was sure which way the relationship was heading. NOW, I think I'm going to keep the sources of my dates confidential too. (Yes, I'm paranoid.) Am I being ridiculous?

-- Josh

Dear Josh,

Paranoid? Ridiculous? Maybe not. On the one hand, ultimately, you do want your friends and your dates to intermingle peacefully (also, platonically); on the other, arguably/strictly speaking, your dates and where you score them are none of their business in the first place. The entire subject doesn't have to be expressly off-limits; it's just that you can dish without data.

About divulging Friend's past with Woman #1, though, you're right: evil. I know your ego took a direct hit. A total, huge, "It is you" slam. But let Date Maul take over, and I promise you, you'll feel not only hurt, not only evil, but also pathetic. Worst of all.

RIGHT?

Also, don't tell your friend that you basically just placed what amounts to a pretty winning personal ad at breakupgirl.net.

Love,
Breakup Girl

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