'Whether you choose to initiate the conversation on a dating app or face-to-face with someone you're interested in, it's always important to have a great conversation starter in your back pocket,' Kate MacLean, a resident dating expert at PlentyOfFish, tells Bustle. So if you find it difficult to send the first message, it can help to have some good opening lines on hand. Everything feels cheesier and forced when you're trying to get the conversation going, but it's like ripping off a Band-Aid - soon, the hard part will be over and you'll feel so much better. It can feel really awkward to start chatting with someone on a dating app.