Say for instance you feel a little thuggish or want to bust out those baggy hip-hop jeans, San Jose is the place to be. Even though San Jose is 'Man Jose,' there are still a lot of attractive women who frequent the area. The Vault is a good place to go with dancing, except there's a cover and normally a line. One place that's kind of under the radar with a decent ratio of women to men is Loft Bar and Bistro. No cover, good music, decently priced drinks and let me reiterate - good ratio.
Let's say you feel like dressing up a little and pretending you make far more money than you do and you don't live at home with your parents - Santana Row is atmosphere in a box. SR has become a chic, pretentious, yet fun, place to spend all those hard earned Silicon Valley dollars. They have a trendy restaurant for almost every genre. Indian (Amber), Mediterranean (Thea), Asian Fusion (Sino, Straights), Japanese (Blowfish), French (Left Bank), Irish (Rosie McCann's), Italian (Maggiano's), Mexican (Consuelo) and of course, Chili's completes this distinguished list.
In terms of night options - Rosie McCann's started out as the place to be. But like most Irish Bars, the clientele really dropped off. They play good hip-hop, and the drinks are probably the cheapest (for SR standards) on the strip. But charging admission really hurts, especially when you have viable options nearby. Sino's is a great place to drink with a huge lounge area. The women are attractive, and you're more than likely to see a cougar or two. Great music, but no dance floor. Straits is another good option, with a very small dance floor, expensive drinks, except they close at midnight. It has something to do with the residents that live above the restaurant.
A lot of people go to the V Bar to close out the night, but it's lame and has the most unnattractive people and worst ratio on the strip. It's dark though, so if you have a blemish you're concerned about, or quite simply, not very good looking, head to the V Bar inside Hotel Valencia. Fortunately, I have extreme beer googles so it doesn't matter what I look like or anyone else I hit on. I prefer to make my embarassing drunken advances to close out the night at Blowfish. It's got a really small bar area, but it's livelier than V Bar.
But let's say you want to be somewhat yuppie or preppie. Palo Alto has a good scene, thanks to an infusion from local Stanford University. There's great food in downtown PA and great places to 'woo' the women, or at least attempt. Nola is good for a pre-drink meetup to discuss strategy with the fellas. From there, move on to Blue Chalk for your conquests, a place I like because it has a spacious dance floor and an upstairs area to just hang out. It's casual and relaxed with a good mix of people. Rudy's is a little more 'gangsta', kind of sketchy, but we always seem to end up there at the end of the night - for what reason, I don't know. There's always 4 women dancing and 30 guys standing around the dance floor.
OK, OK, you want to just put on some tennis shoes and have a few drinks with some friends who make horrible wingmen anyway - head over to Campbell where all your beer needs will be met. Katie Bloom's is the best place to go with a good ratio. They actually do have dancing, but the majority of people hang out at a booth talking or stand around watching the people dancing. King's Head is the place with the most space and room to hang out with the chaps, either on the large patio or inside. The drinks are cheap and if you feel like cougars are still too young for you, than you'll have plenty of options here. Don't go to Khartoum's - horrible ratio and violent guys who just want to fight because there are no women around. Although, if you like watching fights, I see one everytime I'm there. Cardiff is the more upscale place in Campbell. They play high-energy, trance music and the place is packed.
Finally, if you feel like going to the least diverse place in Silicon Valley, head over to downtown Los Gatos, where people either choose not to dance or can't. Probably the latter. There's like one place to go with a dance floor and that's Mountain Charley's. There's a cover and it's pretty crowded. Check out Black Watch down the street. It's a total dive, but they serve these Kamikaze shots that they give to you in mixer that you pour yourself. It's cheap, there's darts, and the people you meet come as they are.
Whew.... that was a lot of material. In summary, San Jose is very hip-hop, Santana Row pretentious and high end, Palo Alto yuppie, Campbell blue collar, and Los Gatos white. In general, I think places with a dance floor are always the best place to 'court' the opposite sex. Bars and lounges just don't have the level of interaction that make it a conducive atmosphere to just walk up to someone and talk. Always ask a woman to dance and never just go up behind a girl and start 'freakin'. I hope this helps for your future philandering.... it hasn't for me.
The Silicon Valley Bachelor
P.S. In fact, the most success I have can be found at Jack in a Box at 2am - where 2 Tacos, a Sourdough Jack, and 3 Egg Rolls never say no to me.