Cold feet about the proposal

Hi Meredith,

I have been dating a wonderful girl for just under two years now. Since I first met her, something about her just sparked with me. We are one of those couples that can hang out almost every day and always have a fun time (even though we sometimes seem annoying to friends of ours). Unlike past relationships I've had, we hardly ever get in arguments, and when we do, it's small stuff that we talk through a day later and get over without resentment.
I just bought an engagement ring and plan on popping the question around Easter. But all of a sudden I feel like I'm second guessing my decision to propose. Now I know this seems like a standard case of cold feet, but hear me out.

One thing that has come up in our years together is our past relationships. After two seriously disturbing relationship events in my past (walking in on a cheating girlfriend in the act, and finding out my first love slept with multiple "friends" of mine), I have a hard time trusting women. She hasn't given me any real reason, other than finding out once that an ex-boyfriend was trying to still hang out with her (she declined his request). But every now and then when we aren't together for a night or two, I start getting suspicious, and my mind starts racing. I basically just think worst case scenarios and start thinking she is cheating on me.

My question is: Should I figure out my trust problems before asking her to marry me (even though I truly feel they are all in my head)? I don't want to mess this one up. She is truly a keeper, and I really want to live my life with her.

– Cold Feet, Boston

Hold off on the proposal. There's no need to rush, so you may as well wait until you're comfortable asking the question.

Something tells me that after more time together, your past with the exes will become ancient history. It's been two years, but it sounds like you're still getting used to your new routine.

While you wait, talk to your girlfriend about the future -- where she sees the two of you in five years, where she wants to live, what you might be doing together, etc. If you're mapping out your life as partners, the engagement won't feel like a big risk. Eventually, it'll just be a part of the plan that you've come up with together.

Readers? Cold feet? Should the letter writer propose now or wait? How can he get over the past? Help.

– Meredith