Dating in general is nerve-wrecking. If it is your first time going on a date with a woman, if you haven't gone out in a while or if one of you is not officially "out," it can be harder still. But by being yourself and picking a safe and fun venue, your date can go more smoothly than you expect and may turn into a second date.
Make sure you pick a public and safe venue for your first date. You may want to tell a close friend where you are going just in case. A coffee shop or casual restaurant will present a relaxed atmosphere where you can actually hear each other speak. If a public space worries either of you because you are not used to dating other women, just be honest with one another. You can assure each other that it is just a first meeting to get to know one another and you can be as low-key as you want.
Try to relax and be yourself during the date. Be confident in yourself and think about your positive qualities without coming across as conceited. On the other hand, don't belittle yourself either. You can tell her details about yourself but don't be overly personal. Talking about exes is generally taboo. If you feel like you don't click with her, still be respectful and friendly.
Figuring out who pays the bill can be awkward. Generally it is etiquette for whoever asked the other to go on the date pays. It is sometimes easier to go to a cafe on your first date so that you each get your own beverage as you arrive. If you would like to foot the whole bill you could say in a friendly way that she can pay the bill for the next time. Some women like to go dutch, whereas others like to take turns paying for alternating dates. Do not focus the conversation too much around finances as it can put a damper on things. If you are paying the bill, do not study it for a long time.
Every situation is different so it is hard to gauge what proper etiquette may be for the first kiss. If you feel a mutual attraction and chemistry, then a kiss at the end of the first date may happen naturally. Approach it with a sense of humor as first kisses can be awkward and make sure she feels at ease and not disheartened. Do not pressure her to give you a kiss or to do anything physical. Make sure she is comfortable at all times.
If you don't feel chemistry with her once the first date is over, do not leave her questioning. It is appropriate to call the next day and let her know whether or not you would like to go on a second date. You may not be sure after the first date if you are compatible. Give her a chance and if after the first kiss or several dates there is still nothing there, be honest with her and don't lead her on.
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