Cache him if you can
I recently discovered that my boyfriend of four years has been secretly searching for his ex-fianc online. I'd say most girlfriends check their mate's cell phone or Internet history, so I think I'm not alone in looking. When I confronted him, he said he wasn't trying to make contact or anything, he just never got closure, and wonders about her sometimes. (About eight years ago, he caught her cheating on him, and they haven't spoken since.) Now I'm all jealous, and feel like I'm competing for his love. Does he secretly feel like he lost "the one"? Isn't Easy Being Green
If your boyfriend's next girlfriend thinks he's being kind of forward on the first date, chances are it isn't because he's trying to find the clasp on her bra; he's just looking for the transmitter. And his wistful glances out into the moonlight? He's checking for the agents in the bakery truck running the voice-print analysis to see if he's lying.
Yeah, you read right. His next girlfriend. If he wrote me, I'd tell him to break up with you, or at least put you on probation and rig his keyboard to give meddlers a little electric shock. You're the guy's girlfriend, not his Net Nanny. You have no right to snoop in another adult's stuff and no, not even if you're really needy and insecure (perhaps the real problem). If you suspect your boyfriend of some misdeed, you get to ask him about it, period. In general, you figure out how your partner feels by paying attention to what he says and does, and by assessing whether you're more like "two bugs in a rug" or "two bugs trapped under a glass."
As for your defense "most girlfriends" violate their boyfriend's privacy lots of people used to think the world was flat, and blacks and whites shouldn't marry each other. In fact, it seems the majority drools more often than it rules. Meanwhile, your big discovery is that your boyfriend sat at his desk and unsuccessfully Googled his ex; you didn't find him dry-humping her on your couch.
Do you know how many people look other people up every day? Their old next-door neighbor, the suspected pedophile down the block, exes they never want to see again? People would've been Googling people in 1786 if they could've. Instead, they had to ask somebody passing through town, and maybe learn the answer, not 2.6 seconds later, but 16 years later, when the guy came back on his horse to return whatever they gave the neighbors leftovers in before Tupperware.
Maybe your boyfriend sees a future with the ex, or needs to make peace with the past, or maybe he hates her and wants to see if she got fat. Worry less about what your boyfriend thinks of other women (which you have zero control over) and more about what he thinks about the newly revealed unethical you.
From my perspective, you should only have a person in your life who you can have alone in your house with, say, a box containing gold doubloons and a stack of your diaries, and feel secure that he'd use the box as a makeshift stool or as a place to set the shaving kit. (Admittedly, I'd probably stash the notebook titled "Hot Sex With All My Old Boyfriends" somewhere near the bottom.)
The clothes snake the man
I'm 21, but all my friends are older very normal, middle-class suburbanites in their 30s. I have a solid career, a house, car, etc. I also have long, wild hair and tattoos, and dress very metal-band. I attract young, clinically insane/goth/obnoxious types when I prefer older, more stable women. Those women either ignore me or get offended when I show interest. Weirdo Boy
"You can't judge a book by its cover" is actually pretty dumb advice. A cover that's bright yellow and illustrated by Dr. Seuss is unlikely to contain the lost Dostoevsky novel, Raskolnikov Hears A Who! Accordingly, the average divorced suburban matron probably has a hard time picturing you piloting her children around in a mini-van. Sure, there might be older women out there who will see you for the middle-age man you really are under all that stringy hair, but it'll probably take getting to know you.
To put yourself in a position to get known, become a regular at a yoga studio or a wine bar, and join groups where the more mature woman can interact with you over time. Maybe become a member of a book club ideally, one of Oprah's or start volunteering; say, at a homeless shelter. Granted, the volunteer corps won't be as rife with eligible 30- or 40-something women. On the bright side, the homeless should be a lot less interested in discussing the allegedly divine secrets of the Ya-Ya Sisterhood.