Overwhelming Pressure from Dating

Dear Edahn,

Fresh out of a spoiled relationship, I've been starting to get asked out on dates by a few men. I've noticed my initial response to this all has been one of discomfort -- I'm afraid to commit to a date with any of these guys because I'm afraid of the expectations he may have about my agreeing to do so (like sex, hooking up, a follow up date, or simply that by showing up it means "I am more than platonically interested"). I know I'm ready to date, it's been a few months since my last relationship ended. But for some reason (and this mentality plagued me on a smaller scale when I dated prior), I can't help but feel overwhelmed with pressure and/or uncomfortable. How can I get over my mental block and start dating?

If I'm understanding you correctly, you're interested in sex, hooking up, and a follow-up date (not necessarily in that order) but don't want to feel like you're required to do those things, right?

There're a lot of reasons expectations can get in the way of you enjoying yourself. You might feel pressure to act in conformance with those expectations, abiding by all the formalities and unspoken "rules" of dating. You might be worried about letting the guy down after he's formed expectations. You might be worried about getting rejected and what that'll do to your sense of self-worth. Any and all of this stuff has a tendency to make people self-conscious about the impression their giving off. Not so fun, but there are some things you can do to help keep these expectations from seducing you. Here're a few ideas.

1. Acknowledge that expectations are just part of the dating process. You are putting yourself out there to be evaluated and to evaluate someone else, but remember that you're not being evaluated as a human being, just as a compatible mate. If you get rejected, fuck it. It might hurt a little, but really, it's not a reflection on your self worth. It's just a compatibility issue. The same goes if you reject him. He's not a bad person, he's just not your taste. You're all still fundamentally good, caring people. If you need any proof, just look for his and your inner child. The more you date and contemplate this, the less personal rejection will be and you won't be as worried about having expectations.
2. Prepare some good rejection lines. If having to let the guy down is worrying you, prepare a little strategy. If I'm not interested at the end of the date, I'll usually say "I had a really nice time, [and the sex was great]" and then send them a text or email after a few days saying that I thought they were very cool but not not a love match and wish them luck. It connects to the first point of not rejecting the person as a human being, just as a mating partner.
3. Acknowledge with expectations with some humor. He offers to buy you coffee, you say "sure, but this doesn't mean I'm having sex with you tonight, got it?" in a really serious tone, then crack a smile and tickle him. Bonus points if you add "unless you buy me a biscotti too." If he has any class, he'd buy you 10 biscotti and bring them back to the table without offering an explanation.
4. Add a disclaimer. You could say something like "I just got out of a relationship and I'm not the best dater. I'd like to get to know you a little without any expectations if that's alright with you." I personally would love to hear something like that. It's honest and refreshing, and I like the idea of building a relationship via an innocent friendship. 
5. Trust in yourself. If you still feel unsure of yourself, that's okay. Being unsure of yourself doesn't mean you won't be able to handle whatever happens. You can admit that there are expectations out there but still know that you can manage them and still be alright. It may not be spectacular, but it'll be pretty good.
6. Trust in your date. If you have good chemistry with a guy, the expectations won't seem like such a big deal. A good date feels more like playing than a super serial mating interview. If you still feel enormous, uncomfortable pressure at the end of the date, it's probably not a great match.

Read this stuff and think about it. Remember it's okay if you're hesitant; most people feel somewhat uncomfortable with the pressure of dating. You can feel a little hesitant and still go on a date and see what happens.