But when you think about it rationality, instead coming from a fear based mindset, you realize four possible outcomes can happen when you approach him. All of them have positive outcomes in their own ways:
1. He's a nice person and you get to chatting up with him and he's friendly and receptive of you. This eventually leads up to the first date
2. You approach him and while he seems like a nice guy he's not a good fit for you. You walk away from the experience with a smile because you know you over came/ are over coming your fear of rejection. It only gets easier from here.
3. You chat and hang out. Before you know it you have a new friend! Maybe not a boyfriend but at least a new friend. If you think you have poor social skills you can practice them with him.
4. He ignores you or blows you off for whatever reason. While that was bad and a blow to your self confidence you can now sleep well knowing ahead of time that he's a jerk. You've dodged a bullet of developing a toxic relationship with this person.
The above outcomes would happen in places which I like to call "social spaces" (bars, clubs, basically, cafes, small classes, organizations. Basically anywhere that fosters socializing and meeting people) That's not to say that you can't meet people while doing errands or going about your daily activities- you can but the chances are slim.
Don't try to play aloof and cool, this is not only a turnoff but it can make the other guy think you're not interested. Instead be freindly and open, drop a few compliments.
Everyone likes a compliment and a smile anywhere they are. You can compliment someone on their speech, on their posture (this has happened to me numerous times), something you overheard, an item of clothing, a drink, a dish, or a book they're reading (see this all the time on public transportation).
Context of course matters about how you approach guys.
For example if you're on an architecture tour make a comment about the architecture of buildings, the event, the people, the tour guide, or the scenery. It gives the person a reason to agree, to joke, or make a sarcastic remark. Something to engage eachother and open the doors to a conversation. If they like you toss a flirtatious response their way. They'll most likely toss one back.
If you're at the supermarket ask about a new brand, ask if they can reach an item for you, ask which isle they found an item in their shopping cart from, ask about a vegetable you're not familiar with, etc.. This is a good way to not only approach someone but it teaches you a conversation starter can be as simple as almost any object.
What about if you're out at a bar? Alone? Well, ask someone what they're drinking and order it, compliment their phone (in this tech era everyone has their cellphone beside them at the ready to make or take a call), talk about the game on TV (if you're at a sportsbar), ask them if they went to your high school and tell them they remind you of someone from back then, etc... Have follow up comments ready to go if they are receptive of you. If they aren't interested be respectful and move on. Don't force anything.
[Sidenote: if you're looking for a long term relationship or want to date someone bars and clubs might not be the best locations to seek these kind of people out]
New in town? Ask for suggestions on finding a good dry cleaner, a bookstore, or a good contractor, a good restaurant. Tell them you've recently moved here and they might be more receptive to you since everyone knows how it feels to be new anywhere.
What about in a new class at school or college? While it's sometimes daunting to approach someone in a big lecture openers work in just about every class size.
Ask someone you're interested in if there was any homework last night, if you want to study together for the exam, what they think of the professor, just get the other person talking to you if you're shy by asking questions, getting their opinion about something or giving them a compliment. Remember compliments, opinions, and questions usually can draw people into conversation and engage them as long as they are done in a friendly, and respectful manner.
If someone is mutually attracted and interested in you it doesn't really matter what you say unless it's very offensive, rude or ridiculous. In fact, an introverted shy guy making the effort is considered cute by some of guys. Keep in mind everyone's shy to varying degrees when they approach someone they're interested in; even extroverts. ;)
Nonetheless, go a bit out of your comfort zone and approach a guy who's eye flirting with you because you might be glad you did. You'll be able to gauge them by not only what they say to your openers but how they respond and especially from their body language.
BTW, speaking of eye flirting I'll have a post on body language next time.
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