We are living in a digital world, and it can make dating, flirting and any communicating pretty treacherous at times! While technology has opened up endless opportunities to meet, connect, and stay in touch with others, it has also created entirely new possibilities of overstepping boundaries and embarrassing moments. I recently had a matchmaking client accidentally send an off-color meme to a woman I had matched him with. They had been having great banter after their first date, but that oops turned her off. How do you date and flirt while making sure you aren’t jeopardizing your budding relationship? Let’s break it down. Texting Texting is an amazing tool! It allows you to connect with people all the time in a way that is not intrusive. When I started dating in the dark ages, you had to suck it up and call them (well, call them back). The endless ringing phone call was nerve wracking. What if they didn’t answer? Were they avoiding you? Do you leave a message, or call back at a later time? Texting eliminates that stress because you can send your message off without worrying about interrupting anything. The problem with texts? They are one sided and have no tone or inflection. How many times have you had a conversation via text where it was completely misinterpreted (although you know what you meant)? Sarcasm and humor can take disastrous turns when you are just getting to know someone. Here are three quick tips to texting while flirting and dating: 1. Keep it short and sweet. Nothing heavy should go in a text. Ever. Texting in the beginning stages of a relationship should be limited to fun banter, or confirmation of plans. That’s it. Everything else should be said in person. 2. No naked pictures. Ever. Sure you can send off a shot of you smiling, or your bedroom eyes, but keep all body parts to yourself. I don’t even suggest sending x-rated shots between married couples. You never know where they could end up, and unless you are a reality star, it will not benefit you. Want more tips on sexting, check out my recent Access Hollywood appearance here. Don't pull a Weiner. 3. Don’t expect an immediate reply. Just because they didn’t write you back within five seconds doesn’t mean they aren't interested. Not everyone is tethered to their phones, and a little time between texts is completely normal. 4. Keep and open mind. If you are just getting to know someone, don't read too much into their texts. This is especially important if they are remotely sarcastic. Confused about something they said? Write back with a question mark, or ask them. Many times a budding relationship can be detoured by an miscommunication over a text. Email Email is another fabulous way to stay connected. However, the same issue arises as with texting, as you can not insert tone and inflection with the written word, no matter how many emoticons and exclamation points you use (I am completely guilty of overuse). At some point, you have to get offline. Just keep in mind the following: 1. Know when to stop the chain for the day. It should never go on indefinitely. At some point you need to say “Talk to you later” or “See you soon”. Preferably before the conversation jumped the shark. 2. Check your “To:” field carefully. How many emails have you gotten that weren’t meant for you? It happens all the time, especially with most mail programs “guessing” who you want to email after you type the first letter. Just double check. 3. Do not expecting an immediate reply. Similar to text messages, it is tempting to expect someone to reply immediately. Keep in mind that they have a life, and might be at work. Give them 24 hours. 4. Always remembering that your email can be shared with the click of a button. The power of the forward is immense. Never send anything that you wouldn’t mind shared. One additional rule about email is to never ever use your work email for your personal use. You don’t own it, and your employer can very easily access your very private messages. Use your personal phone to send messages – even free email accounts can be recorded real time.