As always, I'm going to start with a caveat: no one thing works for everyone. You have to know yourself, and obviously differently people operate differently. Here are just a few random tips that I've picked up along the way.
▶︎ I've seen it where people get so paralyzed by "I'm not sure if I really like this person! Maybe I should stop dating him/her." Perhaps because of the desperation factor for many, they may keep dating someone they should have let go a long time ago. On the flip side, people may break up too quickly, because there is something superficial that is bothering them.
There is no timeline. Dating someone is not commitment to marriage. The only commitment in saying "yes" to go out again is the commitment of one more date. Instead of dating with the mindset of "Do I want to marry this person?" In the beginning, try working with, "Do I want to spend more time with this person?" If the idea of sharing another couple hours with your date is appealing, go for it. If it isn't, you need to ask yourself very seriously why not and if you should still be going out.
▶︎ Don't be afraid to be vulnerable, and let the other person know what you're thinking. It's always a positive practice to communicate effectively. Shidduch dating can be stressful, especially when there's a third party go-between that is micromanaging the relationship. Being open and honest with each other is extremely important toward building a healthy relationship. If you have an issue with something that happened or something that is going on, talk about it. Keep things simple; say what you feel, and don't beat around the bush. (And IMHO here, things work a lot better when you communicate directly to set up dates. You're both adults; you can handle it.)
▶︎ Don't be afraid to be vulnerable, and let the other person know what you're thinking. It's always a positive practice to communicate effectively. Shidduch dating can be stressful, especially when there's a third party go-between that is micromanaging the relationship. Being open and honest with each other is extremely important toward building a healthy relationship. If you have an issue with something that happened or something that is going on, talk about it. Keep things simple; say what you feel, and don't beat around the bush. (And IMHO here, things work a lot better when you communicate directly to set up dates. You're both adults; you can handle it.)
▶︎ Don't assume people will change. What you see is what you get. Your date is not your project; you cannot, and should not, try to fix, change, or domesticate someone. Every person needs to be individually responsible for treating the other right, being accountable, committing, and staying connected. One of you can't carry the relationship alone. If you're uncomfortable with things each other do while you're dating, or your relationship dynamic, it's a red flag. These things don't change after you get married.
▶︎ Throw out your "list," and stop vetting your dates against what you are "looking for." That's fine to do while you are evaluating whether or not you want to go out with said individual, but once you're already dating him/her, stop trying to check off boxes. Does it feel right? Do you share the same values? The person you end up marrying may not match that picture you had in your head all your life, and that's okay! (Also, stop comparing him/her to other people you've dated. It's not helpful.)
▶︎ It's always a good idea when you're ending a relationship to define why. If you had a good run, even if you didn't date each other that long, but you got emotionally involved, try to talk things out and clarify what happened. It will help you later if you have thoughts about trying again. More on communication, clarity and closure another time.
▶︎ Pay attention to what people who have your best interests at heart are saying about who you are in the relationship you're in. It's always possible that some people won't "get" the person you're dating. If it's a personal preference type thing, feel free to ignore; however, that's totally different than people saying that they don't like who you've become, or they get bad vibes about the guy/girl. It's usually nearly impossible to be objective, so that feedback is important.
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