Hi Meredith and readers,

I’m in my mid-30s and I don’t know how to date. I have never been one to casually see multiple guys for long periods of time. I have a history of being a serial monogamist. Even when my plan has been to just keep it casual and light, I’ve ended up in a relationship. It’s not a bad thing, but it has set me up for my current predicament.

I met this guy and we’ve been seeing each other about once a week for the past two months. He’s funny, entertaining, successful, caring, and interesting. Our conversations last for hours and we both love learning about each other and spending time together. But we have agreed that because of our mutual history of being “damaged goods” (he has been in two broken engagements due to infidelity on the other party’s part; I was in a breakup straight out of “Legally Blonde”), that we would take it slow and not rush into a relationship, including anything physical. We’ve both agreed that getting physical adds another layer of feelings and emotions that can complicate a new relationship when you’re still trying to decide if you actually like the person enough to invest in them.

Here’s my problem: At this point in my past relationships, it has been a real relationship. I’ve never been in this situation before. I’ve tried talking to other guys on the websites to keep my options open, but no one seems to match up to this guy. I’m still active with friends, hobbies, and work, but I’m constantly worried about how to keep in contact and ask for dates while keeping it slow and not coming across as annoying or pushy. I don’t want to screw this up because I think this could turn into something really good. But I also would like to know what he thinks.

What does slow mean? Is it once per week? Is it just weeknight dates as opposed to weekend dates? Can I ask him to make future plans, like a few weeks out? Can I ask him if he’s seeing anyone else? Can I ask what the timeline is? I don’t want to rush things, but I’m getting more attached and interested and fear getting hurt again. How can I keep this moving forward without scaring him away?

– I Don’t Know How To Date, Central Mass.