Dating involves uncertainty, and a person may worry about rejection for many reasons. If a trans partner mentions past rejection, listen without assuming every hesitation comes from that history. You do not need to promise a permanent relationship to respond kindly and honestly in the present.
Replace vague signals with a clear invitation
Instead of “We should do something sometime,” offer a plan the other person can accept or decline: “Would you like coffee on Saturday afternoon?” If you cannot make a suggested time, explain whether you want an alternative. Clear communication is useful without guaranteeing that nobody will feel disappointed.
The NHS guidance on relationships and wellbeing encourages honest conversation and listening. The examples here apply that broad principle to dating; they are not a psychological treatment or an assessment of anyone's attachment style.
Ask what the worry concerns
Try “What are you most unsure about?” rather than telling the person they are overthinking. They may be concerned about your intentions, privacy around friends or the pace of the relationship. Answer the question you can answer. If you do not know what you want yet, say so without using uncertainty to keep them waiting indefinitely.
Agree a reasonable communication pattern if both people find that helpful. Do not promise continuous contact or access to your phone to prove affection. Reassurance should not require giving up ordinary privacy, sleep or other relationships.
Let disappointment remain possible
You can be considerate and still decide that a relationship is not right for you. Give a clear answer without criticizing identity or presenting rejection as a lesson the other person needs. Likewise, another person's fear does not remove their responsibility to respect your refusal.
If worries repeatedly disrupt everyday life or make dating feel unmanageable, the person may want support from a qualified professional. Offer help finding it without diagnosing them. For the relationship itself, choose the next honest step: another date, a slower pace, a later conversation or an ending. None requires a promise that rejection will never happen.