How to Talk to an Old Friend over Instant Messaging

Finding Your Friend Online

Find out the person’s online information and request to add them. This can be done through chain mail, by asking other friends or by searching for them on the Facebook search bar or through a search engine. If you don't think the person will remember you, write a short note in the greeting box for the invite to remind them who you are. You might say, “Hi, I’m not sure if you remember me, but we used to attend the same high school.”

Have a look at the person’s profile. Check out their occupation, where they live, and their relationship status. Look at pictures. Find out what they're interested in, and see if you both have any similar hobbies or interests. Any connection points can fuel your messaging conversations and make things a little less awkward.

Wait patiently for an add. Once the person adds you, send your first official message. In most cases, you don’t actually have to wait until the person comes online to message him or her. You can send a message anytime and wait for the person to respond at their convenience. Maybe start off with something short and sweet like “Hey, I haven't spoken to you in ages! How have you been?”

Use the content on their profile to start a conversation. After the two of you have messaged back and forth for a short while, it can be hard to come up with interesting topics to keep the energy going. Also, be sure not to talk about yourself too much. But, at the same time, don't be afraid to include details about you every so often. Keep the balance right. Instead of asking a broad question like “What have you been up to?” be more specific by commenting on a picture or post. For instance, if the person makes a post about their job, send a private message saying something like, “Your job seems really interesting! What got you started in marketing?”

Making a Deeper Connection

Send an email message. If you are messaging the person from Facebook, his or her email may be listed on the profile. Once the two of you have gotten reacquainted, it is appropriate to transition to other forms of communication like email. Send the person a note letting them know how pleased you are to get back in touch. You can use email to pursue other ways to connect like asking for the person’s phone number or scheduling a Skype or Hangouts session to chat face-to-face.

Arrange to meet up, if possible. One way to forge a deeper connection with an old pal is to schedule a time to meet in-person. Choose something low-key and casual like getting together over coffee or sharing breakfast or lunch. If meeting one-on-one makes you anxious, consider setting a date when you can meet up with a group. Reach out to several old friends at once who share a common background to reduce the pressure. This may be difficult if your friend has moved away. If this is the case, perhaps invite them to stay with you for a couple of days!

Send something snail-mail. If the friend you lost touch with was a very close pal, it may be appropriate to send a package and/or letter to the person. Ask for an address and put something in the mail that boosts the connection between the two of you. It could be a postcard if you are traveling, or a small care package of nifty little things that the person liked when the two of you were closer.

Share pictures of your life to catch up. Show them what you’ve been up to! This helps bridge the connection and gives your friend a visual of your life now. Recently graduate college? Send a few pics of graduation, letting her see what your parents and family look like now. You can even take a walk down memory lane and dig up old pictures of the two of you from the past.

Managing the Basics

Consider the reason why you fell out of touch. Keep in mind that the success of your reconnection will depend on the history the two of you share. How your friendship faded away will determine whether your friend is actually open to restoring your relationship. Prepare yourself for backlash in the case of a friendship that ended badly. For instance, your friend may still have bitter feelings about an issue from the past. If things ended badly, you may want to prepare a statement to address any previous problems you two had. In one of your initial messages, you may want to apologize for any past indiscretions.

Show authenticity in your motivation for reconnecting. Another factor to consider is your reasons for wanting to get back in touch with this person. Be honest with yourself about your motives. Are your motives genuine for trying to reconnect? Make sure that you’re interested in rekindling the friendship for positive reasons.

Keep it casual at first. Any early interactions should be time-limited and pressure-free. This allows the two of you to keep it light and friendly while keeping expectations low of where things may go. Also, keeping things casual enables the two of you to decide how you want to move forward.

Be prepared for your attempt to crash and burn. Sometimes, trying to find a spark in an old friendship is hard. There’s a chance that it won’t go anywhere, and that’s okay. Don’t take rejection or failure for the connection to go deeper as a sign that there’s something wrong with you. People change, and you two may not have very much in common any longer. Whatever the reason, be proud of yourself for trying and keep moving on with your life.