My old flame: I’d like to try again

Dear Guys,

I’ve been seeing a guy I had a long term committed relationship with again. Okay, here’s the deal….we were together for about 6yrs. I broke up w him as we were both going through some fairly serious “issues/changes”. That was about 6 yrs ago. Recently, about 4mo ago, we got back in touch. We decided to go into a FWB(Friends with Benefits) type relationship as he had ended a 3yr relationship about 5 mo prior. PS-issues have been resolved for both of us… Upon first discussion I said that I would want to know if he were sleeping with anyone else and he stated, “Ignorance is bliss, I don’t want to know.” Well, after about a month he sort of pitched a fit because he “heard I was seeing someone else” and “wanted to see if I would tell him.” HUH?!?! I was not sleeping with anyone else and the problem was talked through.

So, things continue to progress. He began to text me daily and frequently. Now he sleeps over once a week and we do breakfast. We ALSO go out to dinner or I’ll cook. Sometimes we hang out w NO sex. We cuddle and then spoon during sleep. He always kisses me goodbye on the mouth, with hugs, too! We usually see each other 2-4x wkly.

The other day he texted me while I was at work, 15 min after his Gramma passed. He wanted to tell me about his awful day.

At any rate, about a month ago I realized that I had feelings for him again. We have a LOT of history and now that we both have our lives on track, I’m really happy getting to know him again.  I’m about being honest, so I emailed him last week on my way to work one morning and told him this. I don’t want to change anything and I know he’s not sleeping with anyone else. Well, imagine my surprise when he responds with some blather about being sooooo busy and not having time for a “relationship” or to be a real “boyfriend.” (His quotes, not mine) He said I’m obviously more than a FB friend, especially considering our history, but he wants to keep it casual and that I should be honest with myself.

WOW! Considering the way things were progressing, this was NOT the response I was expecting. I was very clear with him in that I don’t want things to change, but it was only fair that I told him about my feelings and that I need a minute to reassess what’s happening between us. He told me to take my time and he would respect whatever I decided. I gave it a week and sent him a casual text saying “hi” which he responded to.

Then (same day), his phone broke and he made it a point to message from FB(Facebook) saying he “was NOT ignoring my texts, if I sent any” and he was hoping for the replacement the next day. We messaged back and forth a bit yesterday and I haven’t heard from him yet today- although it’s not quite 9am! LoL! Now, i just feel strange and unsure of what’s happening…how to progress or if I even should.

At any rate, I’m beyond confused. Any help would be appreciated. BTW, we’re both in our mid 30s. I need an unvarnished opinion from some actual men on this one, please help!


Dear S,

Thanks for writing to us.

We can understand how you both wanted to tread lightly at first seeing that you have a history together-one that didn’t work out the first time-and also seeing that you’re both coming out of other relationships. But now that you’re seeing each other so much the lines are blurred, and what seemed to be working for both of you is now only working for one of you.

In some ways his reaction makes sense because he’s already getting all of his needs met. You see him four times a week, and in many ways already act as his girlfriend, but with no real commitment. This is great for him, but a recipe for disaster for you.

Even though this feels complicated, the best thing to do is tell him how you feel. Yes, he may run, but only if he doesn’t feel the same way about you. Lots of women think guys don’t like to pressured. And while that’s true, we’re no different than women in that way. No one likes to feel pressured. But it’s only pressure if we don’t want the thing you’re presenting to us. Example: If you said to him, “I really want to have sex with you a lot.” Do you think he would feel pressure? Absolutely not! He would say, “Bring it on.”

So be straight with him. Tell him how you feel and that you’d like to give it another try, if that’s what you really want.

You won’t get him back by acting all casual and pretending that things are cool the way they are. Too many people try this approach only to be resentful later. Don’t sell yourself short. Go for what you want. If it doesn’t work out you’ll have no regrets. And if he says no, then you’ll be free to find someone else who values who you are and wants to be with you.

Good luck.


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