How can I get over fear of rejection in romantic pursuits?

Dear Fearful of Rejection,

Dating can be nerve-wracking, and it’s admirable that you’re trying to understand why you have these dating-related insecurities. No matter the type of relationship, romantic or otherwise, there's always the possibility that you’ll fall for someone and risk being rejected or that others will fall for you and you'll need to figure out how to turn them down. Some self-reflection and taking steps toward improving your self-esteem may be the key to landing yourself a wonderful, mutually satisfying relationship. 

The first step toward understanding is awareness—and you seem to be well on your way! Whether single or dating, your experiences may provide opportunities to learn about yourself, other people, and your relationship preferences. You mentioned that your generally positive view of yourself turns negative when faced with dating and the possibility of rejection. You also recognize that you're the most comfortable in a stable relationship and you prefer to hang out with people you already know pretty well. It's also worth pointing out that you seem to feel self-assured and outgoing when you're hanging out with your friends. Since you feel confident and outgoing when the pressure's not on for dating, you may find it useful to think about what is different about the beginning of dating compared to being with friends or in a relationship. 

Once you’ve had an opportunity to reflect on where you're at emotionally, it may be a good time to remind yourself what you have to offer. You may start by making a list of your strengths and positive qualities. What are some of your proudest accomplishments? What are some of your happiest memories, and why? Where do your passions lie? What makes you, you? You could even ask some of your friends to share some of the qualities they most value from your friendship.

Just as dating can be considered a process, building self-esteem is also often a process. It’s not uncommon for people to feel self-assured in one situation and self-doubt in the next. This process of building self-esteem involves precisely the sort of critical thinking and inward reflection you're already doing. If this is something that you continue to struggle with, you may try talking with a mental health professional about other strategies to reduce your fear of rejection.

To your point about the interactions you have with your male friends, maybe you’re looking to them to provide comfort during your singleness. Maybe they do see you as a sister or mother figure, but it's really hard to say unless you ask them directly. It could also be that they just dig you for you! In any case, it's good to have supportive friendships. Since you have a great social support network, it could be easier for you to find some date-able partners through those connections.

Your ability to identify your situation and willingness to work towards a resolution is already a great start. Here's to building the confidence to take a chance on love!