I’m in my early 30s and just started trying cold approaches... maybe 15 attempts so far with 5 dates and one instadate (which was a huge ego boost at the time, but I thought she was just okay) over the last two months. Those 15 attempts were a lot of prep, and mentally exhausting... I’m fit, well put together and have a good job... but I feel like I’m behind. Most guys I read seem to be doing this are in their 20s and it makes me feel like I’m way behind the curve.

People tell me I look younger when I shave... like 25 to 28. That helps my confidence a little, but I still keep thinking about the "half your age plus seven" rule. I don’t want to seem creepy or out of place... it’s really messing with my head.

I’ve had moments when I see a cute girl... whether she’s taking photos for a shoot, walking with her parents, or anything else that doesn't seem as opportune as standing waiting for someone/reading texts. Sometimes I can go 45 minutes at a busy event without seeing someone I find attractive and a moment feels right. And when I do see someone, there’s a difference between thinking she’s cute and her being someone who’s really my type (which is maybe once a day if I am really going out there). Even then I can just psyche myself out and just leave a bumping area or event because I am nervous to jump into these more unpredictable circumstances or not seeing anyone that exciting. I don't want to seem like I am barging into their life.

So I’m wondering... should I start approaching girls who I don't find that appealing really? Maybe it would help me practice and get more comfortable before going after the ones I really want to talk to.

Anyone else started cold approaching later in life? How do you deal with the age factor and not let it stop you? And do you think I should go for women I’m not as attracted to just to get more experience with approaching? How do I go about situations where a girl I find very attractive but the situation isn't as condusive to an easy approach?