Dating is one of the biggest aspects of life, and as such it is one of the most common topics in therapy. In particular, issues regarding approaching someone you are interested in are very common. One of the most common issues is people not knowing how to approach a person they find attractive.

We learn a lot from our parents, but dating usually is not something we learn from them. It’s also difficult to learn from our friends because we don’t always have their personalities.

The right way to approach someone is to be process oriented rather than goal oriented. Instead of trying to get a date, get a girlfriend/ boyfriend, or even just score, you need to view it as getting to know another person. As long as you see it from this perspective, it stops you from performing an act – instead, the main aspect of your encounter becomes sharing yourself with another human being. Here is a homework assignment for you: go out and have a good conversation with any girl or guy you think is attractive, but person-to-person, with no agenda other than just enjoying the conversation; don’t even consider asking her/ him out for coffee. When you get used to the concept of engaging in a continuing dialogue with strangers – having the audacity to shift from just sitting in a coffee shop to having a full on natural conversation about the coffee, the weather, her/his shoes, or whatever topic is present in the moment – you can move on to the next step.
Get out of your brain. You do not need to try to be perfect, right, nice, or smart. It will make you very anxious. Being caught up with yourself will hide your sexual energy, the component of you that creates attraction. Your anxiety and thought processes will stand in the way of that sexual energy and your ability to be flirtatious. When speaking to someone you are interested in, you need to be present and comfortable in your own body, speaking about the same things you would otherwise, except feeling and embracing your sexuality within the context of the conversation. This will change your natural body language, causing it to express nonverbal cues communicating your interest to the other person. If this ignites the other person’s interest, you will naturally enter a phase of flirtation and excitation, where you communicate via spoken word and body language both. As a result, it will become easier to ask someone out casually, working along the lines of “we’re enjoying this conversation so much we should get together to continue it.” At the next conversation you can move to the next level and ask for a date.
From a girl’s perspective, there is a cultural idea that girls have to be asked out rather than doing the asking themselves. Girls can be assertive if they want, but it is far more common to be pursued. So, even if they are interested in someone, they won’t convey that interest directly.
People at a slightly older age might be looking for a more permanent relationship. Sometimes, they end up dealing with the dating process as if they are evaluating portfolios, rather than just enjoying the process, assessing who their date is, and figuring out if they could have a good relationship with them, they treat it almost like a job interview. This approach doesn’t work for two reasons:

One, by treating a date like a job interview, the fun aspect of dating gets diminished. Treating a date like a formal interview inevitably prevents you from getting another date.
Two, people are not usually clear on what they want; being unclear in an interview setting can be very awkward, while being clear to yourself with what you want will allow you to evaluate your date in a more casual manner.
One way you can get clear on your own is by listing out 100 items of what you would want from an ideal relationship – not just your partner but also the relationship itself. Maybe the first ten to fifteen items are cliché things we all want, then another 15 are a bit more specific, coming from things you’ve learned from past relationships and the people around you. Then the stretching begins. You need to observe other people, ask friends and family, read books and watch movies, and figure out what you really want. Thus, you go from wanting “this size, this tall, kind, loving,” to what type of relationship we want: clear communication, honesty, security, e.g.. When you write the list of 100, you see how much you yourself fit into your ideal relationship, what you want to offer and what you yourself bring to the table. Of course, you don’t bring the physical list on dates, but the act of thinking about what you want helps you naturally figure out if your date is a good match.
The time you spend going out with someone is for the sake of the idea that you are going to meet with another human being and find out whether this human will match what you want for a date or not. Even if you’re looking for the perfect job, you don’t treat any interview for a less than perfect job as pointless; you treat each interview as if it’s the exact one you want. You should do the same thing when dating. Like interviewing for a job, where there is a lot you can learn just from the process of going through interviews, there is a lot you can learn just from going on dates. You enjoy the process, bringing your thoughts, emotions, and sexual energy to the present moment. Different parts of you get shared, then you sense if the same thing happened for the other person. The date itself is about getting to know someone and enjoying the time you spend with them. However, subconsciously, you have things that you want out of a relationship. In order to have a good relationship, you need to become consciously aware of what you really want; the more you do your own homework of your own needs, likes, and dislikes, the more apt you will be to share and ask on a date in a natural way.
It should be noted that these issues are not gender-specific; it isn’t only men that have trouble approaching someone they are interested in, and it isn’t only women who have issues with evaluating their dates. These issues come up at different points in your life, and it is important to be able to recognize and deal with them if you want to have a happy relationship.