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Dear Harry:
Regarding Valentine Day in five days, since neither one of you takes it seriously, maybe a casual celebration-like of the day will be adequate to both- you can put some humor into it, and this might not need much time to prepare.
It is wise of you to be cautious. It is a risk to get emotionally attached to a person- you could get hurt, and the hurt may feel really bad. So, it makes sense to get to know her better- like you suggested. Get to know her before committing. Most people of any age, don’t bother to do this. They jump into intimate relationships with people they basically don’t know. Once intimate, people can no longer get to know the other objectively. Emotions get in a way of clear viewing and thinking.
Get to know her before committing and before becoming physically intimate.
Your concerns are valid- as you know there are no guarantees, but you can greatly minimizes your chances of getting hurt and maximize your chances to have a healthy, loving experience by going about this wisely.
anita