I wish he had a car – and a different job

Hi,

I'm a 44-year-old professional woman with a slew of failed, short-term relationships, and only a couple of long-term ones. I've experienced some pretty big emotional and physical traumas, and I'm sure the way I think about and handle relationships is all really screwed up.

I recently met someone who is 12 years younger. He's smart and sweet ... and he has no car and works full-time as a bartender, which means he's around a lot of "partying," which he's told me himself. He seems really responsible but he definitely drinks quite a bit, and since I have had issues with alcohol, this makes me wary. Am I am shallow in wishing he had a car at this point in his life, and a better job? One that wasn't so centered on drinking? We are not at the point yet where I am having to drive him around, but I guarantee if that ever happens, I will become resentful.

As far as his job is concerned, I just didn't see myself dating a younger bartender at this age, and I feel like a jerk judging him for his job, but as I mentioned, it's contributing to what I think is more drinking that should be done (for me and him). And finally, the age difference: I know it should not bother me, but it does a little. I feel like it shouldn't. On the flip side, so far he is treating me really well and he seems kind and thoughtful, so I don't want to just toss him aside. It's so rare that I connect with someone who I think is decent. Thoughts?

– Shallow?

You're not shallow. You're asking fair questions about what this relationship will be like in the future.

And that makes me wonder: What does he think about his job and lifestyle? Does he enjoy the partying or is it just part of the job? Feel free to ask him what he likes about his work. It's better to know why he enjoys it, because that will let you know why he might continue.

You say you haven't hit the point where you're driving him around, but I want you to know that you never have to do that. Every relationship has boundaries, and you can be clear about yours. You don't want to be his car service. Also, you're not going to be comfortable joining him in some social situations because of the drinking. All of that is OK. You can say no.

For the record, there are a few red flags here that suggest this isn’t a forever relationship. But it sounds like there's some good stuff, too, and that you'd like to know more. Something to consider: Does this have to be exclusive right now? You might have an easier time figuring him out if he isn't the only person in your life. If you continue dating others – or at least stay open to it – the stakes might feel lower. There is no need for them to be so high right now.

– Meredith

Readers? Shallow? Too many red flags?