I went out on a date the other night. The woman is a new hire at work. We are in different departments at a big place with more than 200 employees. Anyway, since she is new, some of her paperwork did not go through correctly. As a consequence, she did not get paid on payday. I know this is true because she was in the HR office talking and she was pretty upset about it. I told her not to worry and that I would be happy to buy her a drink. We had already made plans to go out, and since I did get paid, I figured what the hell.

So, we went out to a bar, and we got a couple of drinks, and I paid. And things were going fine: no lulls in conversation, no weird ex-boyfriend stories, no obvious warning signs. She even seemed like she was having a good time and that she might actually like me. But then she’s like, “Let’s go to another bar!” And I was thinking, “I don’t really want to spend any more money,” but I didn’t know what to say, so I agreed, and we went. And she drank kind of a lot, getting louder and wilder as the night wore on. She drinks whiskey, by the way, which is very attractive in a woman but very expensive, as well.

I guess I should explain here that I don’t make a lot of money and that I live alone in an apartment in a city. It’s not like I’m starving, but I have to be careful with my money. She is basically in the same boat, so it’s not like a Some Kind of Wonderful, "different side of the tracks" thing, either. After the second bar, she wanted to get food, and then we went back to my house where she promptly passed out in my bed and snored all night like a buzzsaw. I slept on the couch. I drove her home the next afternoon on my way to work.

So, now I don’t know what to do. It was kind of a disaster, and I don’t really think I want a repeat, though she swears the next night will be on her. Of course, she left her bike at my house, so now she has a reason why she needs to come back sooner or later. I can’t decide if I should just politely extricate myself from this situation and try to maintain a civil yet distant work relationship, or go out a second time and see if things improve. I do OK with the ladies and all, but it’s not like they’re beating my door down, if you get my drift. Is it possible that this was just first date awkwardness to the Nth? Or should I run away from this situation and go back to video games and beer?

Well, you said that things were going well at first, right? You had plenty to talk about, attraction seemed mutual? Maybe let her take you out after she gets paid and see how it goes. It is possible that she was nervous and drank more than she would have. It is also possible that she wasn’t thinking about the cost because she told herself that she would get you back next time. That said, you might have suggested a cheaper route yourself, you know. If you were getting out of your comfort zone, you might have suggested going back to your house and making some food? I don’t know. Just a thought. It seems like you like her, and from what you’ve said, I think this is more likely a case of her not thinking about the money than not caring. I say give it another shot, and maybe food before drinks next time?

I have been dating a great guy for several months. We are both divorced and in our 50s. I have three kids (grown up and moved out) and am on good terms with my ex. He has no kids and doesn’t really see or hear from his ex, who lives in another state. This is important to me because I have dealt with enough of other people’s family drama for this lifetime and have no desire for more. Anyway, as I said, things have been very good. I have my other friends, many of them male, and hobbies and pursuits, and so does he. He owns a small house, and I have the same apartment I have lived in for over 10 years. We can go to whichever place we choose, and we usually spend the night together at least three or four times a week.

Well, here’s the thing. The other night, he mentioned the possibility of us moving in together. I tried not to react, but inside I was panicking. And the thought of it now just fills me with dread. It has nothing to do with him, I swear. I just really, really like having my own place. And I don’t know if I ever want to share a house with anyone again, but if I do, it will not be after a few months of dating. I don’t know how to approach this, because I don’t want to hurt his feelings and I would really like to continue dating him, but now I find myself getting anxious at the thought that he will bring it up again. What should I do?

Solitary Woman

Is it possible that it was a moment of exuberant affection that passed and he might not bring it up again? Like a drunk, post-coital, “I wish we could stay here in bed forever” kind of thing? Is it possible that he read your silence on the matter and won’t bring it up again? If so, I think you should leave it until he brings it up again. If not, then you probably need to have a real talk about this as soon as possible. If he wants things to move faster and there is no possibility that you will change your mind, then better to get the talk over with before things go any further.