Should I take this huge risk?

iVillage Member
Registered: 07-08-2005
Should I take this huge risk?
2
Wed, 11-08-2006 - 9:25am

I have liked this guy since grad school.That was about 13 years ago. We've had little affairs (he had a gf) but I did not wait around, I started dating other people. We've been friends even through my marriage (divorced now) and his moving far away (he came back 5 months ago) He's had this fiancee for 3 years in a very disfunctional, long distance relationship. This ended a couple of weeks ago. He's said he can see himself with me being happy and having a family. He's said that he would like to try to date and see what developes with us. I've had strong feelings for him in the past but we've never had a chance to date. Either he's dating someone or I am. We've never been "single" at the same time. There's a LOT of chemistry between us and we have a LOT of things in common. We always have a good time and have a lot to talk about.

Currently I am dating someone new (2 months) and the relationship is ok but I wonder if we have enough things in common (we have different interests for example I like to go out more than he does and he has a LOT of hobbies that I don't share)It makes me wonder.

Now my friend is single and I think there might be a chance we could try things out and get it out of our systems. However its a big risk. What if he doesnt develope feelings for me? He has said that the reason he hasn't been "in love" in the past is because of timing and being with somebody else. But isn't love "inconvenient"? Can it only grow under certain circumstances? Is this worth a try?

Should I end a relationship that is good to try something so risky? Should I ask him how he would feel if I broke up? Should I wait for him to get out of rebound? NOw this question is a little tricky. Yes, he might be on the rebound, even though he chose to end the relationship. But, he's just like me, we go from one relationship to the other. And already he has friends that want to introduce him to his siblings or friends.

I'm afraid that the window of opportunity is open now and that it won't stay that way for long. I'm afraid that the same thing is going to happen all over again, we'll end up dating other people. I'm also afraid he will hurt me by not being capable of falling in love with me (he hasn't in the past, although now he sees me different, he sees us getting married).

Help please!!!

SodaSplash

iVillage Member
Registered: 11-21-2003
Wed, 11-08-2006 - 7:26pm

It's a huge risk I tell ya, AND the most important thing, which I consider a red flag is the fact that you both had affairs while dating other people. You both have a pattern to look for something or somebody while you're both supposedly committed to somebody else. Have you seen this pattern throughout the 13 years? Nothing can guarrantee that he'll be faithfull OR that you'll be faithfull while dating each other.

If you're in a 2 month relationship now and doubt it, then break it up and start dating your friend. You both being single will make it easier for everyone involved and won't hurt others feelings. If it doesn't work at least you'll have it out of your system.

iVillage Member
Registered: 05-31-2005
Sat, 11-11-2006 - 10:38am

Though I'm all for risks, I don't think this is a wise one. You've both had affairs, he's just gotten out of a relationship and is already talking marriage? Doesn't that set off alarms for you?


Personally I don't think there's a lot to gain here... maybe in a few months time things will be different, but right now? No.