Before you ask him out, consider whether you and he are ready for a monogamous relationship of a more serious nature. After interviewing over 700 of the oldest Americans, Cornell University professor Karl Pillemer determined three key questions can really shed light on whether someone is right for you. As Pillemer recommends on "Psychology Today" online, ask yourself, "Can we be friends?" "Do we like each other's family?" and "Can we talk about everything?" The answers to these three questions can help you decide whether you should move forward, or whether you need more time before getting serious.

Prepare yourself for the impending discussion with your guy. On his website, VibrantMentalHealth.com, cognitive behavioral therapist Bernard Bilicki suggests that you mentally ready yourself for a serious relationship discussion by writing down your thoughts on a notepad. If you think there might be any roadblocks to your guy wanting to move forward in your relationship, Bilicki recommends writing them down as well, and noting any possible solutions. Psychologically prepare yourself for the conversation by focusing on what you hope to achieve and by deciding ahead of time to respect your guy's point of view regardless of his answer.

When you sit down with him to have this serious conversation about your relationship, tailor the discussion with him in mind, recommends "Women's Health" magazine in the article "How to Talk to a Man." This means starting by telling him that you want him to be your boyfriend. Then, tell him why you think a monogamous relationship is the right step for the two of you. Guys are much more attuned to nouns and verbs, and picking up nuances isn't generally one of their strong suits, warns "Women's Health." Don't be afraid to be direct with him.

Before you talk to him, be ready for the possibility that he might not have an answer for you right away. This doesn't necessarily mean he's planning to reject you. If he wants some space, give it to him, suggests certified professional coach David Kanegis in the Huffington Post article, "My Man Won't Commit, Why Not? 8 Critical Questions!" Move on to another topic of discussion or an activity. Kanegis even recommends calling him the next day and telling him that you have a family commitment and won't be able to see him for a week; however, he warns that this approach can be "risky" and that you should speak with a therapist or wise, trusted confidante before trying it. After this time apart, if he's in the right place for commitment, he may come back with a positive response, asserts Kanegis.