Test the proverbial waters by asking the guy about his thoughts on relationships. Avoid making your discussion an interrogation and instead, make the occasional lighthearted comment about your feelings on relationships. You’re testing his readiness to respond in a positive way if you ask him to be your boyfriend but you’re also reducing the risk of rejection. In the midst of a text conversation, pick a relevant comment and build on it. For example, if you’re discussing movies, ask him “What movie would you choose to take your girlfriend?” This both opens the door for further discussion and lets him know that you have thought about being his girlfriend.

Ask him out on a date. If you’ve been able to ascertain his level of interest in being your boyfriend by asking him his thoughts on relationships, you can further test his interest by simply asking him on a date. Keep in mind that you don’t have to officially label it a “date,” which can be too much, too soon. Instead, asking him “Hey, I was wondering if you’d like to catch that movie we’ve been wanting to see.” This offers the same outcome but with less terrifying implications if he isn’t ready to be your boyfriend. Ideally, he will understand that by your asking him to join you alone in this activity, you think of him as a bit more than a casual friend. If he doesn’t, it’s a good first step.

Convey your feelings towards him, in texts. If there is a challenge in text communication, it’s the lack of nonverbal cues that tell far more than the words you speak. Although you probably don’t want to be aggressive in explaining that you want him to be your boyfriend, you also don’t want to be vague. One of the best ways to identify your feelings to someone is to preface your statement with “I.” So, for example, saying “I really enjoy talking with you and I’d like us to spend more time in person together,” puts your feelings out there in a way that isn’t overwhelming but is clear.

Communicate with him regularly, using compliments and emoticons. Compliments enhance your feelings of well-being and they support another person’s confidence, notes psychologist Raj Raghunathan. Similarly, emoticons are the technologically driven approach to what is missing in texting: nonverbal cues. Adding a smile or wink to your compliment is the text version of flirting. This approach also gives you an opportunity to gauge his responses. If he responds in a similar way, with compliments and emoticons, it’s a good bet that he would also be receptive to your asking him to be your boyfriend.