Tag: ask my best friend on a date

To those who choose to date in their friend circle, here’s some personal advice…

During the last few months, I’ve decided to stop being a wimp and ask out the friends I’ve been interested in for a long time. But naturally I was very worried about ruining good friendships. However, I had many great experiences, going on dates with those guys, realizing there wasn’t a mutual spark, and still maintaining a solid friendship afterward. Granted, it’s still a bummer on both ends when there isn’t a spark. But neither of us can say, “What if…?” anymore.

But it really grinds my gears is when the expected drama ensues. So here’s some advice I had to learn the hard way.

Let’s say you’ve already been on a date with that friend, and you’re interested in a second one. Be prepared for them to not return that interest. In fact, they may not know how to turn you down, so they may choose to say nothing at all. They might go so far as to avoid you altogether. This is in no way your fault and you can focus your energy on someone who WILL care about you, even enough to say, “I think you’re great, but I just want to be friends.” Because you at least deserve that much.

But keep in mind, that person may come crawling back for another chance. Proceed with caution. If they rejected you the first time, quite often they come crawling back because they’re looking for temporary validation and believe you’ll care enough to give it to them. You are worth so much more than being someone’s second choice or after thought. Because usually, those people get over it very quickly, and will walk away from you again. Or during that time, they’ll want to keep it a secret from your mutual friends. They might go so far as alienate you from them so it won’t make them look bad. In this case, tell anyone you feel comfortable confiding in. You don’t want your friends turning on each other, which can be avoided by saying things like, “They’re horrible because they did this…” and perhaps replace it with, “I’m sad because this is what happened.” And to the friends who are listening, their hurt is very real and only want someone to listen. You might have information that will give them some peace of mind, and that they’ve been treated isn’t personal. Often, that’s what they need to hear.

Now if the circumstances are less dramatic and look a little more like this…here’s my advice to you. If the friend you asked on a date says yes, make sure you set up a date and time for when this will happen. If you say, “Let’s do something this week” there’s a chance that might not register fully. It might go so far as to finding out come Friday night, that friend was with someone else.

If that person WAS with someone else, do not say passive aggressive things like, “The party turned out to be lame. Hope you had fun with your date.” They’ll likely take it as a sincere wish, or understand your upset quickly defend themselves. In the later case, you could end up apologizing for getting irrationally upset. But the truth is, you’re feelings aren’t irrational. You’re upset because you had said, “Let’s do something this week” and they hadn’t been paying attention enough to make that mental note.

If you choose to say something about it, best case scenario, they’ll make an effort to set up a date with you. Worst case scenario, they change the subject and end the conversation right there. The last thing they want is for you to be upset with them, so they might hurry to reassure you, preventing your negative feelings from escalating, and just avoid it in the future.

That can often lead to another week going by and they’ve stopped acknowledging you altogether. By now you probably feel a bit gipped, and that’s warranted. You’ve likely seen how they’ve treated the people they’ve liked and made an effort to pursue. They took them to fun places, showed them genuine affection, and made them feel special. It’s very easy to start comparing yourself to them, which takes a heavy toll on how you value yourself.

But you might choose to give them the benefit of the doubt and give them more time. You even ask directly, “When are we going to go on that date?” and they say, “I’ll think of something.” But once again, if no solid plans are made, the way you value yourself diminishes a whole lot more. And so at this point, you have two solid choices. The first would be to let it go, because sometimes avoiding conflict is the best option. But if you choose to be honest about what’s been bothering you, here’s my advice to EVERYONE in this scenario.

Confrontation is scary. We sometimes enter it thinking we’re going to get an apology, or that person will immediately change and provide what you asked for in the first place. But most of the time, they will respond with their own prepared defense, and will do anything to avoid facing your anger and upset. It’s a very realistic and human response, which can’t be held against them. But if you find yourself with more anger than you know what to do with, say it! But of course, say it without the purpose of cutting them down.

Avoid, “You did this to me” or “You’re a terrible person because…” Instead, try, “I’m upset because this is what happened between us, and this is how it made me feel…” And if someone is upset with you, listen! Their hurt is very real and deserves to be acknowledged. They cared about you more deeply than you did them, and that isn’t going to go away over night. It may require some action on your part, but an apology goes a long way, and compromising has a great way of saving friendships and relationships. But more importantly, it lets that person you know you really DO value you them at a person; that you value them the way GOD values them.

And sometimes, relationships will end. People will choose to walk away altogether and there’s nothing left but to respect that decision. But at the very least, you did all that you could, and that person will move on a lot quicker than they would have holding a silent grudge.

To wrap things up, I think it’s safe to say I’ve had my fair share of experiences. Don’t get me wrong, I’m very happy and grateful for what I have, but being single has its set of lonely challenges. Many broken relationships, unwanted drama, and everything in between. It’s a bumpy ride, but at some point it’ll all be worth it. Until then, cheers to my fellow YSA’s who receive some peace of mind knowing I’m right there with you.

Cheers to you, XO

~Chelsea

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