Notice the expectation
Sometimes a plan carries an unspoken rule: kissing should lead to sex, sex should include penetration, or an orgasm should prove it went well. Try saying the rule out loud. Is it something you actually want, or something you feel obliged to deliver? You can agree on a different plan together.
Use a more useful question
Instead of “Are we doing this properly?”, ask “Is this comfortable?”, “Would you like something different?”, or “What would make this more enjoyable?” These questions leave room for an answer you can use. They do not require a person to produce a particular bodily response.
Let bodies be variable
Sensation, energy, interest, and physical responses can change. A particular response is not proof of how attracted someone is, and arousal is not consent. If a change concerns you, you can talk with a qualified clinician. In the moment, a partner can listen to the person rather than interpreting their body for them.
Make a smaller invitation
“Would you like some closeness with no expectation of anything else?” can be easier to answer than a whole evening that seems to have an outcome attached. Be honest about what you mean, and honour the answer. Affection also needs to be wanted; it is not something a partner must offer in place of sex.
Afterwards, ask about experience
Try “What did you enjoy?” and “Is there anything you’d change next time?” You can appreciate connection without rating the other person’s body or describing the encounter as a success or a failure. A useful conversation can include enjoyment, uncertainty, and the things you chose not to do.