How To Ask A Guy Out When He’s Fresh Out Of A Relationship

Typically, it’s not a good idea to bombard someone with love the second they leave a relationship. That being said, if you really like someone and the opportunity suddenly presents itself, it may be hard to resist. Guys who just got out of relationships may be a little fragile at first, but if you keep that in mind, you may be able to score a date or two. Here are the best approaches to take if you want to ask out a guy who just left his girlfriend.

  1. Acknowledge the heartache. You probably know how it feels. Even if you’re the person who made the call to break up, it still hurts. Breakups can be awkward, and only a few of them end without any type of hurt feelings. Before you ask him out, tell him that you’re sorry to hear the news. Then, you can always throw in the hint that he’ll find someone else very soon because he’s such a catch.
  2. Give it time. If you approach him too soon, you’re just going to be a rebound. Chances are, you want something more than that. Be there for him, keep communicating with him, and ask him to go places with you in a non-romantic context. Let him get to know you and see how much fun you are. Hanging out with you may help him officially get over his heartache.
  3. Try to make sure you don’t fall into the friend zone. If you’ve been hanging out with them a lot and haven’t made any sort of move, you’re destined to fall into the friend zone. While you want to get close to this guy, you want him to see you as an option — and not just a bud. So, try to flirt a little when you can. Playfully tell him about bad dates you went on since it’ll give him a chance to visualize you as a romantic partner. Plus, it’ll give him an opportunity to ask you on a date that’ll be much better.
  4. Promise not to stalk his ex on Facebook. That’s just creepy. Whatever his relationship was like isn’t much of your business, and if you accidentally mention specific facts about his ex, he’ll get scared off. Don’t get involved in the past if you want to have a future with him. Even if you’re curious, you need to respect what happened between them and not pry. He’ll also feel more at least in dating you next since he’ll see you as a completely clean slate.
  5. Tap into his interests. If you’ve always wanted to play guitar and know he’s a pro, ask him for tips or lessons. By showing him that you have something big in common, it’s a great way for a future relationship to blossom. Learning about something he’s into is also a great way to get some unique conversations flowing. Maybe by class #3, you’ll feel confident enough to ask him out on a date.
  6. Write him a letter. Have you had a secret crush on him for a long time? Maybe the best thing to do is write it out. Just make sure to keep it light, especially if he doesn’t know you very well. Tell him what you like about him and mention that you’ve always thought he was a great person. Say that you’d love to get to know him better, but also understand if it’s too soon based on his recent breakup. Getting it all out will be therapeutic, and it’ll put the ball in his court, which is helpful.
  7. Get a vibe from his friends. If you have any friends in common, they can be key in setting something up. For one, they’ll be able to figure out how heartbroken he is after ending his last relationship, and gauge whether or not he’s ready to move on just yet. Secondly, they’ll be able to give him hints that you’d be worth pursuing. Yes, it’s technically having someone else do the work for you. But if they get back to you and say he’s not ready yet, you may avoid humiliation or heartbreak.
  8. Send him a gift. It could just be a bag of gummy worms if you know they’re his favorite. Attach a note that says “thinking of you,” and make sure to include your name. If the two of you aren’t already friends, this will leave him intrigued as to who this thoughtful stranger is. If you are friends, he’ll feel good knowing that he’s on your mind. Small gestures can often lead to really happy results.
Karen Belz is a New Jersey native who is currently living in Maryland. She has a Bachelor’s Degree in Speech Communication with a focus in Broadcasting and Print Media Studies from Millersville University of Pennsylvania. Since graduating, she has written for sites like LittleThings, HelloGiggles, and Scary Mommy and is currently an e-commerce editor at Bustle.

When she's not writing, she enjoys making her phone run out of memory after taking too many photos of her dog. You can find her on Twitter @karenebelz or on Instagram @karenbelz.