The biggest hurdle faced by many budding portrait photographers is the need to find amazing subjects to collaborate with. Reaching out to and communicating with models can be intimidating, but it really shouldn't be, as it can very easily lead to a very rewarding collaborative shoot for both parties.
This isn't fifth-grade recess where you are hoping the model notices you are interested in working with them. The first step to actually breaking that ice is by reaching out and beginning a dialog. Don't dig into your online dating toolkit or any sort of manipulation scheme. Instead, be straightforward, honest, and professional. If you are communicating digitally, make sure to communicate in full sentences that are free of slang and emoticons while also being careful to use correct grammar and spelling. Show the model that you take every step of the process seriously and want to bring professionalism from start to finish.
Have a Concept
Virtually every model is constantly beset by new photographers asking to shoot. Surprisingly, however, very few of them actually have an idea. Rather they just want to shoot or do some variation on a casual shoot where the model just shows up at a location and snaps some photos. Your goal is to stand out and catch the models attention. An interesting concept that will help him or her push their modeling in a new direction is a great way to do so. Show the model that you have taken the time to actually craft an idea that has vision and interest. This will separate you from the masses of other photographers out there yammering with just: "Let's shoot sometime!"
Have a Creative Team
The first time a model works with a new photographer requires that the model take a tremendous leap of trust. One of the best ways to both show that you are serious about your trade and also not a predator is by finding a creative team to work on the shoot with. When initially approaching the model, let them know that you will be supplying a creative team containing perhaps a makeup artist, hairstylist, and/or wardrobe stylist. This will help the model feel more at ease and worry less about shooting with someone they have never met. Make sure each member of the creative team has an online portfolio the model can evaluate.
Have Relevant Work
This one can often be one of those chicken/egg scenarios where you need to work with models to have relevant work to show models to get them to work with you. This is fair, but always try your best to show the model as many relevant examples of your work as you possibly can. If you have a portfolio full of landscapes and are all of a sudden emailing a model to shoot pin-ups, then you will raise some eyebrows and come across less genuinely. If your portfolio is completely empty, it might be worthwhile investing in a few workshops before reaching out to models. At a good workshop, the teacher will not only provide you with amazing education, but they will also supply models for you to work with so that you can at least craft the beginnings of your portfolio.
Be Willing to Pay
It probably isn't realistic for a new photographer to pay full modeling fees for every shoot while they are first getting started just as it isn't realistic for models to pay photographers for every image while they break into the industry. This is why models and photographers learned to collaborate. When collaborating, however, expect to work with models of a similar experience level to you. A highly experienced professional model doesn't have much to gain from working with a new photographer looking to build a portfolio, which means collaboration won't be appealing to them. You can, however, accelerate your growth by working with models beyond your experience level by hiring them. Always remember that regardless of whether or not you are planning to work collaboratively or not, both parties always should be paid for their time. Sometimes that payment is in the form of portfolio images, other times that payment is in dollars, but don't expect a model to ever work for free just as you should never work for free yourself.
Often, the biggest challenge for new photographers looking to connect with models is only fear. Don't let fear of rejection or failure stand in your way, or you will never get anywhere. Instead, take a stand, wearing your professionalism as armor. Use it to break that ice and take the next step towards creating the images you have always dreamed of. Nothing is standing in your way except yourself.