January 25, 2010 2:08 PM Subscribe
Help a late-blooming dating newbie figure out the mysteries of entering a relationship.
posted by anonymous to human relations (11 answers total) 20 users marked this as a favorite
Inexperienced late-20s male trying to get back into the dating scene. I had some issues with shyness/introversion and fear of intimacy when I was younger that kept me from building the sort of basic dating/sex knowledge and experience most people my age have formed. I've done a good job of getting over the introversion the past few years to form some solid friendships, but dating is still a bit of a mystery, particularly the fine art of crossing over from "friends" to "dating".
One of my biggest issues is flirting - as odd as this sounds, I feel like I need basic instruction or coaching in this. Although I can sort of do this when I'm relaxed and enjoying myself, I often come off as overly serious or distant if I'm nervous or don't know the person well. In other words, when I first meet most women I'm interested in. Any suggestions to make myself more fun to be around, flirty without being too obvious, and more engaged would be welcomed.
Another issue I've had is interpreting signals. I have a number of female friends who seem to be have this playful/flirty way of speaking and writing when they talk to ANY guy - how can you tell if they're into you, or just being their usual flirtacious self? For example, a girl I recently met that I've become rather interested in e-mailed me after I gave her a ride last week, basically saying "thanks...maybe we could hang out sometime. If you're ever bored, you've got my number :)" She tends to be a bit flirty in e-mails though, which leaves me wondering if she is indirectly asking me out or if she literally just wants someone to hang out with.