Contacting Her
Approach her in person. If you happen to run into her in a public setting, you can choose to simply walk up to her and start talking to her. This by far the most direct approach, and might take some guts. However, you can definitely do it and pull it off with a little luck. When you approach her: Stand straight with good posture. Don’t act like you’re nervous or uncomfortable. Smile. Make sure your clothes look nice. Act relaxed – as if you have plenty of time.
Text her. Texting is great because it won’t really be in her face. Ultimately, she’ll see the text and then be able to respond (if she wants to) on her own time. However, when texting her, remember to keep it short. In addition, don’t ask to hang out with her right away. Instead, engage in some light banter, joke with her, and ask her how she’s doing. You could start off texting her something simple like "Hey! Long time, no talk." She might respond she doesn't know who you are, and then you can take the conversation from there. If she does know who you are, ask her how she's doing. Consider texting her about something you think she finds interesting. For example, if she's really into politics, say you were watching the latest election results and thought of her.
Contact her on social media. There are many ways to contact her on social media. You could send a message (keep it short), like one of her posts (on Facebook), or simply comment on something she posts or says. In addition, you could also tag her in a photograph – reminding her of the good times you once had together. Tag her in a photo and write,"Good times!" If you message her on social media, send her something short like, "Long time, no talk. What's going on?"
Call her. Calling her is very direct and could be awkward. However, it could also be the simplest and easiest way to reestablish contact. Ultimately, you need to make the decision as to whether you want to contact her in a direct way (like calling) or in a more indirect way (like texting or on social media). If you call her, you may want to start off by honestly explaining yourself. Introduce yourself and then say, "I remember that good time we had last fall, and I was wondering what you were up to." If you call her and she doesn’t answer, don’t call back. Leave a message or a missed call. If she wants to contact you, she will.
Starting the Conversation
Re-introduce yourself. If you’re calling her or approaching her in person, you need to introduce yourself. While she might remember you, there is a good chance she might not remember your name. Take the opportunity to briefly introduce yourself. In addition, remind her of how you know each other. Say something like “Hey, Ann! I’m John – we know each other through Andy.” Don’t be offended if she doesn’t know your name or forgets it later.
Use humor. Whatever way you decide to contact her, you should consider using humor. Humor will make a potentially awkward situation funny, and help remind her of your virtues. There are many ways you can do this: Start with a light-hearted joke about something you might think is funny. For example, if you remember she really likes Oreo cookies, you can joke about those. Joke about fashion. For instance, say “I was just in the mall and saw someone that looks exactly like you wearing crocs.” Use self-deprecating humor. For example, say, “Hey, do you remember me? The guy who wears the absurd cowboy boots.”
Ask her how she is doing. Contact her and start up a conversation about how she’s doing in life. If you’re interested in a romantic relationship with her, this is a good way to find out if she is available. In addition, this is a very honest and straightforward way of reinitiating contact. Generally, you can say something like “It’s been a while since we spoke. How are you doing?” If you knew her from work, and one of you has moved on, ask her “So, what’s going on with work these days?” In the case you knew each other through a mutual friend, you could simply ask about whether she’s spoken to that person recently.
Don't pretend contacting her is a mistake. It will seem disingenuous.
Meeting Up with Her
Invite her to an event. Whatever way you contact her, invite her to an event you’re attending or hosting. This way, it will seem that you are interested in her, but it won’t be too forward. By inviting her to an event, you’ll give her the opportunity to meet you in a low-stakes situation. If you’re throwing a party with roommates or friends, this is probably a good time to reestablish contact with a girl you might be interested in. If you’re going to an event or party somewhere with a group of friends, reach out and invite her to join your group.
Ask if she wants to join you for something simple. The easiest way to meet up with her is to suggest something that seems fun and casual. This is important, as you’re likely to strike out if she thinks you’re asking her on a formal date. Instead, consider inviting her to join you: For coffee with friends. For a drink at a place you both already hang out. At some sort of event you both are interested in. For example, ask if she’d like to meet you after a concert, or ask if she’ll be going to a certain campus organization meeting.
Leave her alone if she isn’t receptive to you. If she ignores your texts, phone calls, social media messages, or otherwise sends the signal that she isn’t interested in you, leave her alone. Back off completely. Give her the opportunity to contact you. If she doesn’t, she’s not interested.
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