There are a number of things that a concerned parent can do to evaluate the character and intentions of their daughter's new boyfriend.
Plan an evening to meet your daughter's new boyfriend soon after you discover his existence. Make the event very casual and insist that the entire family is present. A nice dinner followed by an exciting board game or two will serve your purpose nicely. Whatever activity you choose, be sure it is one with lots of interaction between your family and the new guy. Note the appearance of the boyfriend when he shows up for dinner. Evaluate how he dresses and whether he shows signs of proper hygiene. Make him wait awhile before seeing your daughter to see if he grows impatient. Remember when you are talking to him, that you are dealing with someone from a different generation, so his interests may not be the same as your own. There are certain things that should transcend the generation gap, though, like good manners, good common sense, and respect for elders. Watch carefully for these things. This is his first test.
Ask plenty of questions throughout the evening and watch his body language closely. Does he seem comfortable with your daughter? Are they overly affectionate in front of the family? Watch how he interacts with everyone and whether he makes eye contact when you speak to him. These things are all important because if he does become a part of the family for an extended period of time, it will be nice to know that he is someone you can trust and who you will want to have around your family.
Keep a notebook and pen hidden in a separate room. Excuse yourself from time to time and write down your observations about the boyfriend's appearance and behavior. Also try to collect information like his name, where he lives, where he works, and how long he's lived in your area, but don't let it seem like you're interrogating him. At some point in the evening, discretely take a few "group" photos that include the new boyfriend so that you will have a permanent record of what he looks like, just in case. Tell him that you want photos to remember the evening and to post in your blog.
Use the resources available to you after he leaves to do a thorough background check. There are many websites available that you can use to search for criminal records and to find registered sex offenders. Don't assume that you can tell whether someone is decent or not by their outward appearance. Find out for sure. Have a serious discussion with your daughter about sex and about your dating rules if you have not already done so. Express to her the seriousness of the rules and be very clear of the consequences for breaking those rules.
Plan another evening with the new boyfriend out in public at a nice restaurant. Watch for signs of chivalry from the young man. Does he hold the door for your daughter and for other people? Is he polite to waiters and waitresses? Whether he ends up paying for his meal or not, does he offer? Try to spend some time alone with him, away from your daughter, and see if he tries to make conversation with you. Always be nice, but throw a few curve balls at him and see how he responds.
Keep very open communication with your daughter about her social life and be familiar with her friends, their interests, and where they like to hang out. Encourage her to always talk to you when she has a problem or when she needs advice. If you decide that her new boyfriend is not right for her, tell her your reasons, but let her make her own decisions. She may not take your advice, but if you demand that she no longer sees him, you can rest assured that you will quickly push her towards him. On the other hand, if you discover good things about the new boyfriend, tell your daughter and commend her on choosing a good guy. Whether she acknowledges it or not, she does value your opinions and by communicating both good and bad information with her without interjecting strong emotions, you encourage her to confide in you no matter what. Above all, enforce the rules established about dating with her whether you like the new boyfriend or not so that your daughter does not lose respect for your authority.
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