DEAR HARRIETTE: I reconnected with a high school friend recently, and we went out for some drinks. The problem is that my classmate treats me like I am still in high school. While I was in high school, I was not the most popular, and I was what some would call "weird." So while we're having drinks, my classmate referred to the strange things I did, and it made me feel bad. I ignored her while she laughed and reminisced. By the end of our meeting, I did not feel like it was a good decision to meet with her. She wants to have drinks again, but I don’t want to. I want to tell her I'm not that same person from high school, and I need her to respect the woman I am now. How do I do that? -- Not the Same 17-Year-Old, Louisville, Kentucky
DEAR NOT THE SAME 17-YEAR-OLD: It is time for you to speak up for yourself. If you have any interest in getting together with this person, you owe it to yourself to let her know that, just like her, you are no longer a high school student. Tell her about yourself and your life. Further, make it clear that you do not appreciate her harping on your behavior from years ago. Suggest that if the two of you intend to rekindle a friendship, you should build it on a bond that you create today.
DEAR HARRIETTE: I work at a small bar, and I see a lot of customers every day. We have a group of regulars and some newbies. One regular comes in and always orders from me. We talk about his job and life, and after each of our conversations, I am more interested. He isn't married or in a relationship. I want to take charge and ask him out for a proper dinner, but I'm afraid he might deny me, creating awkwardness when he comes to the bar. Should I ask him out? How would you suggest I ask? -- Bashful Bartender, Las Vegas
DEAR BASHFUL BARTENDER: You are right to be a bit cautious here. Sometimes people share their life stories openly at a bar because it feels like a safe space in that there are no ties that bind. It is also true that true love has been discovered in that same setting. If you feel like the potential for a relationship with this man is worth the risk of awkwardness, go for it.
Tell your customer that you want to invite him to a “proper” dinner. Say that you like him and want to get to know him outside of the bar. State that you hope he will accept, but if he doesn’t think it’s a good idea, you hope the two of you can continue to be buddies at the bar. In this way, you will have given him an out if he needs one.
(Harriette Cole is a lifestylist and founder of DREAMLEAPERS, an initiative to help people access and activate their dreams. You can send questions to email@example.com or c/o Andrews McMeel Syndication, 1130 Walnut St., Kansas City, MO 64106.)