Tips to Woo Someone That’s Been Single a Long Time

Sharing for a healthy society.

When someone has been single for a while, they’re totally fine being alone. They don’t need a relationship since they’re comfortable not being in one. They may not love going to bed alone, but they know how to do it and they’d likely rather be alone than put up with the nonsense that can happen with a relationship that just isn’t working.

If you’re trying to start a relationship with someone who’s been single a while, be prepared for someone set in their ways who may not have a lot of time for you. This doesn’t mean they aren’t open to a relationship, but if they’re used to being single, it’s going to be hard for them to adjust to what it means to be in a relationship again.

They may do things without inviting or even telling you. They may want to take things slowly. And they may need a lot more “me” time than you’d expect. And they may be more reserved with their affection and have their guard up for a while.

In order to woo Someone That’s Been Single a Long Time consider the following tips:

Don’t be clingy

Nothing is going to make a single independent guy or gal run more than a clinger. They have been perfectly fine without a relationship for however long, and they don’t need someone, even you, so they are going to be turned off by someone who makes it seem like they’re not okay without a relationship. They will want to know that you can handle being alone because they’re going to need their alone time too.


Let them choose the pace, without controlling everything

After being single for a while. They may want things to go slowly to make sure your intentions are genuine and that you’re someone they can trust, but they may also be so used to being single that they might forget about you altogether.

If you planned the first date, let them plan the next date. But send a gentle reminder text like “Does this Saturday work for you?” if you’re finding it’s taking them too long to respond. You have to be sure that you’re not putting in all of the work. Since that’s bound to make anyone feel resentful but you want to give them some control. So you’re not suffocating them.


Be open and clear

If you’re looking for something serious, make sure your single-and-loving-it guy or gal knows that. Just because they’ve been single for a while doesn’t necessarily mean they want something serious. They may just be seeing what’s out there after a hiatus.

If they want something serious, let them know you understand that takes time to build trust and that you’re willing to wait. You aren’t going to wait forever.


Be yourself

This is always the best dating advice because you want to be with someone who likes you for you and vice-versa. If you don’t like being alone much and want to dive into something sooner rather than later, Mr. or Ms. Solo may not be your best bet for now.

You may need to try out other options or get more comfortable with yourself and being alone instead of pretending you’re on board with something you’re not.

While dating someone who has been single for a while can be a little more work, the important thing to recognize is that. They also have some really attractive qualities: they know what they want. And they likely aren’t willing to settle.


They aren’t going to be dating you as a rebound or to flee their fear of being alone. They’re going to be independent and okay being alone.

Being with them and gaining their trust may take more work. and time but that slow burn might give you the long-term happiness you’ve been hoping for 🙂 🙂

Sharing for a healthy society.

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