Making the Decision to Pursue Them
Find out if they're dating someone. If the person you've got your eye on has already moved on with somebody else, you might need to let them go. Ask mutual friends about their relationship status Check social media for clues Recall if you've seen them out with anybody
Assess why it didn't work before. There was a reason (or reasons) why you rejected them in the first place. It can be easy to ignore these issues if you haven't seen them for a while, or if you're just feeling lonely. But it is really important to acknowledge the concerns you had before, and determine if you can overcome them. Otherwise, you are likely to hurt them again. Did you find them unattractive or annoying? If so, has this changed? Did they hurt you or lose your trust? If so, will you be able to get past it? Were you going through a rough time in your life when you rejected them? Have things changed? Were you simply incompatible? If so, do you think you'll be able to compromise and find balance?
Look for clues about how they feel. If you are still in touch with this person, try to assess how they feel about you. This can help you determine whether or not it's worth it to put yourself out there. Spend some time objectively evaluating how they act when you're around. You might also ask for the opinion of a close friend. Negative signs include: changing their phone number, not responding to your texts, avoiding you. Positive signs include: lighting up when you come into the room, making time for you when you ask, standing close to you when you're out with friends.
Improving Yourself
Brainstorm ways to make yourself more desirable. If you previously rejected this person, you are approaching the situation at a bit of a disadvantage, as they may still have hurt feelings, and this can affect their attraction toward you. You can compensate for this by making some self-improvements! First, brainstorm some ways to make yourself more desirable. Some ideas include: Becoming a better listener Changing or improving your look Getting more in touch with your emotions Making a positive career move Improving your living space
Make a plan. Try to think about how you can be more attractive to this person, and choose that method for improving your life. Once you've settled on a goal, break that goal down into manageable steps. Set deadlines for each step. If you are trying to become a better listener, practice with your friends and family. You can also ask them for feedback to see if you've improved. If you are trying to look better, break this down into different parts. Make a plan to have your hair done. Ask a stylist friend to help you pick out some new clothes. Join a gym. If you'd like to be more in touch with your emotions, schedule some time each day to reflect on how you feel. Start a gratitude journal. Speak with a close friend, family member, or therapist. If you'd like to improve your living space, start by cleaning your space and clearing out clutter. Then move on to organizing your things and adding some decorative pieces.
Take action. After you have a plan in place, you have to start making changes. This is the most difficult (but most rewarding) part of self-improvement. Just focus on each small step at a time, and try not to be overwhelmed by the big picture. As you continue to improve your life, you will become more attractive to the person you want to reach. Choose a start date (no more than 2 weeks in the future) and determine your first step. When that date comes, don't hesitate! Hit the gym, start your gratitude journal, or begin cleaning! Stay motivated by celebrating every small victory. Seek out a community of people striving toward similar goals.
Reconnecting
Send a sweet text. If you are ready to reconnect with them, start by sending a text. This is a casual way to start a conversation, and test out how they feel. If they respond within a few hours, and if their tone matches yours, it is probably a good idea to keep pursuing them. Try not to make it seem like you're looking for a booty call. You could say, "It's been so long since we've hung out. I hope you're well." Opt for a text rather than a call, which can put more pressure on this person to give you an immediate answer. Reader Poll: We asked 720 wikiHow readers and only 9% would reach out to a former flame by calling and sharing their feelings. [Take Poll]
Keep the conversation going. Keep communicating casually via text message for a few days or a week. If there is a good back and forth happening, eventually work up to telling them you miss them. You might say, "Talking with you has been so much fun. I really miss spending time with you." Do not send another text until they have responded to your last one. Avoid sending more than a couple of texts per day. It is OK to take a day off between communications. Respond to any texts from them within 2 hours.
Own up to what you said or did in the past. Even if they seem open to reconnecting, they probably have some reservations. You are going to need to acknowledge any ways you might have hurt them in the past, and try to reassure them that you won't do it again. You might say, "I know I hurt you last time we tried this. I was selfish and scared, and I'm sorry." You could follow up with, "I have really tried to change and improve myself. I like to think I'm a better person this time around." Avoid rehashing every detail of the past. This should be a chance to start fresh.
Start with a casual meet-up. If everything goes well, ask them out for a date. Start with something casual, like meeting up for a cocktail or coffee, to keep the stakes low. You will know right away if it feels like it's working. If you are both enjoying each other's company, plan a second date.
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