I think there's a mentality where you want the best possible conversational outcome. And you're surprised time and time again to find you're only one half of the equation and she just wants an alright conversation.
Video Games, for example are THE FUNNEST THING EVER IN THE HISTORY OF THE WORLD. Some people have not found their genre yet. People who don't try and find their genre are just an example of someone not open to new things.
Once you get INTO playing games (or watching movies, TV or Anime together) it's tough to get out of and go out and see people. However if you're an awkward guy it's tough being around people without them associating awkward sexual motives to you (or rendering you a sexless cheerful teddybear, in danger of having opinions stomped) without a girlfriend to point to. So it's tough either way.
Ideally you have a girlfriend money, and the ability to go out and socialize. But really the three tend to be horribly interrelated unless you really nail it.
My best times were spent with close friends drinking, gaming, and talking. If economies of scale had worked out for gamers there would be LAN parties every night after work. But because games have been marginalized and criticised the laptop industry hasn't really embraced decent gaming graphics cards which has kept gamers attached to their towers. Something that can't be shared with a girlfriend or a group of drinking buddies easily.
Eventually a game will come along to unite the masses. Something not everyone loves, but no one really objects to and that is fun and social. Thinking back the last one I can think of was quake 1. Which had 1v1 for spectators and bragging rights and Random free for all death match. Which was just a giant melee of randomness. That made it so people could focus and not socialize and maybe do a bit better or they could just relax and let each kill or death not faze them at all.
Something like CIVILIZATION 2 would be good, since it has broad appeal is amazingly fun, kind of random. But it's too slow and advantages accrue too fast.