I asked him to stop flirting

We chat today at 1 p.m.

Hi Meredith,

I am in my late 30s and was in a long-term relationship for almost a decade. During my LTR I was very relaxed and trusting of my ex. I thought we had a solid, collaborative, monogamous relationship and that we were mutually invested in its success, and I was actually quite proud that we each maintained a fairly high level of social independence -- we had a very interconnected life, families, etc. but didn't feel the need to spend all our time together. I thought this was healthy. In the end I discovered that he had been cheating for some time, and had also hid compulsive spending from me -- something that almost bankrupted us both. Our breakup was traumatic.

I was single by choice for a couple of years, having taken some time to get therapy, sort myself out, and recover from the emotional and financial toll of his betrayals.

In the spring I started dating a guy I had known socially for a year or so. Because we started as friends, I knew a fair amount about him, and that gave me a baseline ability to trust him -- no small thing for me, I admit.

I also knew that we had a flirtatious mutual friend that he had been attracted to for some time. To my knowledge they never dated, but they had the kind of relationship where if she was in town and they ended up at a party together, she'd end up sitting on his lap at some point in the evening. Maybe they were occasionally physical over the years. It didn't happen too often because she doesn't live in town, but often enough. The flirtatious behavior didn't change when he and I started dating.

At first I didn't say anything to him about it, because we weren't that serious. A couple months in though, when we were exclusive, I let him know that I'd prefer if he would not be so close physically with her now that we had established ourselves as a pair. I also acknowledged that seeing him flirting with another woman kind of stirred up my relationship baggage, and that I was trying to get past it but I wasn't there yet.

He agreed, but I ended up breaking things off with him after he took a couple of weekend trips and wouldn't say where he was going. Turns out he'd gone out of town to hang out with friends, including this woman -- and decided that it was better to not tell me than to be up front about it. I wasn't comfortable with that. It made me feel like he was sneaking around behind my back, and if there was nothing to hide then why was he being secretive?

In a way I feel like I did the right thing by expressing what I wanted and breaking things off when he demonstrated via his actions that he didn't want the same level of transparency that I did. That's fair. The other part of me is angry with myself for not being accepting of their relationship as it was, and letting it become an issue. I guess everyone has someone in their life they hold some kind of candle for, right?

What I want to know is: Do I have unreasonable expectations? How would someone without enormous battle scars manage this kind of situation? What are the red and yellow flags I should be looking for, and what's just me overreacting?

– Not OK, Cupid, Boston

Forget the battle scars for a minute because I'm not so sure that they're relevant. You asked this guy not to get all touchy with this woman, and he responded by lying to you about weekend trips. You never forbid him from hanging out with her, right? You just wanted some respect.

Your expectations don't sound unreasonable to me. You simply wanted your boyfriend to keep this woman away from his lap. If that's how you framed this to him, you managed this situation like a pro. He's the one who should be questioning his motives.

Really, my advice is to stop thinking of yourself as someone with horrible baggage. Sure, your most significant relationship devolved into a mess, but your past doesn't seem to be preventing you from making good decisions about new experiences. Most people would have trouble watching a boyfriend flirt with another woman in front of them. No one wants to be lied to about weekend trips. You reaction to that stuff had very little to do with your ex.

You don't have to bring up your scars when asking someone to make you feel good in the present. You're allowed to trust your instincts -- because they sound just right.

Readers? Should she have ended it? Should he have lied to her about the trips? Is her baggage relevant? Help.

– Meredith