Proceed with caution

All of the warning signs are there.

The girl I am dating just got out of a nine year relationship last September. I knew this before I even met her. See, my aunt decided to play cupid this past holiday season and fix me up with someone she knew from her office. I listened to her and my cousin argue that this girl wasn’t ready for a real relationship. At one point, they stopped arguing and asked me-

“You’re not looking for something serious are you?”.

What am I supposed to say to that? It’s almost as if my own family has stereotyped me. I suppose I deserve it, I have been somewhat of a serial dater the past two years.  Maybe I do want more. Maybe I just havent found it.

Anyway, this girl has been giving out all the warning signals of someone who isn’t ready to get back into a relationship anytime soon. She talks about her ex alot. She accidentally reffered to him as her fiance the last time we talked on the phone. She admits that she is still really close to her ex’s family. She shy’s away from intimate conversations.

Despite all of these warning signs I still find myself interested in her. I know I should proceed with caution but really, thats never been my style. I’ve always been an all-or-nothing kind of dude, in every aspect of my life. I’m not sure that I know how to play things safe. I’m not sure that I would ever want to play things safe. I have never been the type of guy who calculates anything. Especially when it comes to matters of the heart.

So how do I proceed? I have thrown out comments about her not being ready and she seems to reject the idea that she isn’t ready. Even though I know better. Maybe I am setting myself up for failure here…or maybe, I should just be patient?

34 Responses to “Proceed with caution”

  1. alexa - cleveland's a plum says:

    hmmmmm. this kind of screams re-bound to me, and obviously to you too considering you are writing about it here. 9 years is a REALLY long time to be in a relationship and it’s pretty apparent she isn’t over him.

    but here’s the thing, i would totally keep seeing her. who knows what will happen. if you’re interested you’re interested.

  2. Jossie Posie says:

    I say just see what develops…she may not be ready for anything serious but thats okay. If you like her why not try anyway.

  3. Carmen says:

    Kinda sounds re-boundy to me too… I didn’t even put myself out there for about 8 months post my 6-year relationship and I think that was the best thing ever (and I wanted out of that relationship)… because I didn’t want to subject anyone to my possible ‘crazies’.

    That said - if you like her, you like her and as long as you are okay with the ex talk… perhaps patience is the best thing. Anyone who doesn’t come with a big of baggage hasn’t lived a life worth living in my books.

  4. Arielle says:

    I would say that you should keep going with it, but if possible, try not to get too attached. It seems like she is totally still getting over the last relationship and its possible that she’ll snap out of it, but…I guess she also might not. So if you’re really interested, no need to back away but I guess don’t be surprised if it doesn’t work out.

  5. The Dumbest Smart Girl You Know says:

    Hi. That girl sounds a LOT like me. Maybe read my blog to glimpse inside her head…

  6. Kendall says:

    I agree with Arielle wholeheartedly. Which seems mildly hypocritical as, like you, I am an all-or-nothing guy.

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  8. Renee says:

    Dude, that was me in a relationship last year that we both tried to make work, but it just wouldn’t because i wasn’t ready. And he tried to keep it casual and let me talk about my ex, and whatnot, but it got hard for him too. I think if you just let her come around in her own time without pressuring anything serious, you two will be just fine. Like Arielle said - don’t stop seeing her, but don’t be surprised either.
    Good luck dude!!

  9. Angela says:

    The way you tell it, your aunt and cousin only want this girl to get laid to get over her ex. Nine years is a LONNNNG time, she’s not gonna get over the guy in four months. But you can’t help it if you’re intrigued by the girl. I know, though, if I started dating a guy who just couldn’t get over his ex, I’d get tired of it. So just feel her out. Is she asking YOU on dates? Or are you doing all the work to get her to come out with you?

  10. Crissy says:

    It’s got disaster written all over it.

    I’m sorry.

  11. Lump says:

    Nope, don’t get serious with this one. She needs to get laid. That’s all.

  12. Marie says:

    From what you’ve described she’s not ready for a serious relationship and actually doesn’t know it herself. Nine years is a heck of a long time and she won’t be able to move on by dating someone else. Besides she keeps talking about him to you? I’m sorry, but that’s NOT a good sign. She needs time on her own, take a break, figure things out.

    Since you are asking other people’s opinion, mine would be don’t get serious with this girl. You would more than likely get hurt.

  13. Greta says:

    Awe. Patience is truly a virtue, dear Matt.

  14. verybadcat says:

    Hmm. Back in the day, when WH would dump me, I would rush out and find someone else to date. Inevitably, when they tried to kiss me, I would cry. Not sure why, just my flavor of the crazy.

    The first guy thought if he got all super hot and heavy it would distract me. He didn’t get a second date.

    The second guy tried to stop the kissing right then and there and talk about how WH probably beat me and stuff. Yeah.

    The third guy? Just kept kissing me, and stroking my hair (and maybe other stuff), like nothing was really going on. He acknowledged my tears, but they didn’t upset him, didn’t stop him, didn’t budge him from his course of action. Asked if I was okay, I nodded, and we kept on. It took a minute or two for the tears to stop, but when they did? Wow. I dated this guy for a month, and only broke up with him because WH wanted to get back together.

    You have to have the temperament to handle her, you have to have a high tolerance for the crazy, but I say go for it. Just understand that she may run away and come back a few times, as she still is on the rebound………

  15. Chris says:

    Oh man, you are asking for trouble here dude. Run and don’t look back.

  16. Lily says:

    I am in the EXACT same boat. I’m dating a guy who just got out of an 8 year relationship. He doesn’t talk about his ex a lot, though I know he’s still friends with her sister… I can’t say all of the same warning signs are there, but I can’t help but be cautious.

    We haven’t had any major conversations about our relationship or where it’s going, but I’m convincing myself it’s because he’s in Texas for a couple of months for work, so we haven’t had a very conventional start to the relationship anyway. I don’t want to push him into a relationship sooner than he wants to be, but I am also very tired of serial dating and having things drop out after few months. I’m interested to see how this works out.

  17. repliderium.com says:

    proceeding with caution is boring. Jump in- if it goes south at least you can never say you half-assed it.

  18. Your Girlfriend is Ugly says:

    Get. Out. Now.

  19. Erin says:

    Trust your instincts. No matter how bad you want it - she is not ready.

  20. lacochran says:

    “Fiance”?! Danger, Will Robinson! Danger! *waves arms*

  21. Felisa says:

    Hmm well of course it sounds rebound-y and I normally would tell you that you should pay attention to the sirens going off here but I know someone who got out of a 2 year relationship, met a new guy within 2 weeks… AND is still with that “rebound” guy 6 months later… She DID end up talking to the guy about her ex quite a bit in the beginning and she felt bad because sometimes, she made him sound like a rebound guy but the thought that “Hey you know what? It’s not my fault this amazing guy came along right after I got out of a break up. It’s unfair to both of us if I didn’t give it a shot” made her keep seeing him and I really don’t think she regrets that decision.

    So if you dive head first into stuff like this… go for it! But as others have said, don’t be too surprised if it doesn’t work out.

  22. sarahbelledotcom says:

    patience is a virtue.

    stick with her.

    life isn’t meant to be played like chess. don’t think too much, or overstrategize. just let the ball roll.

  23. longredcape says:

    I’m kinda going back and forth on this one. On the one hand, she shouldn’t be penalized for feeling the way she does. Nine years? Jesus. That’s going to take some recovery time. Just make sure she’s not using you for someone to cling to because she’s not used to being single. Make sure she’s in it for the right reasons. Try not to scare her off with “serious relationship” talk, but make sure the relationship isn’t going in that direction if you’re not going to talk about it yet. Does that make sense? I guess what I’m saying is, if it looks like it’s going into the boyfriend/girlfriend realm, you need to talk about it first.

  24. Miz says:

    I seem to disagree with just about everone on this front..go figure!!
    Since you said you were an all or nothing kind of guy, I would delete her number. If, someday, she wakes up and realizes she’s been actin a fool…then GREAT for you (if you still happen to be single). I don’t see what you would gain from spending your time with a girl who constantly talks about her ex and is emotionally unavailable (unless, of course, the sex is outstanding..in which case props to ya..). The girl sounds like a few dozen red flags and a waste of time to me…not saying she’s a bad girl, but we only live once. There’s no need to waste your time on someone who is unavailable! :) Best of luck!

  25. k8 says:

    Look, nothing in love done half-assed is ever a good idea. If you like her and your want to proceed, then do it. Ready, schmedy. If I waited until I was ready for most of the things in my life, I’d be dead.

  26. lbluca77 says:

    If she was in a 9 year relationship and broke up 4 months ago then yes she needs more time. She is just trying to get her feet wet with the whole dating scene, she is not ready to jump in the pool.

  27. Princess Pointful says:

    My secret– I’ve been that girl, to a certain extent.
    And I actually don’t think you should run.

    Honestly, it seems to me that people are putting too much of a formula onto this. If she is the type of girl who has never been single before, and seems clingy– yeah, you’re a rebound, and you should probably run.

    However, I fell head over heels not long (i.e., less than four months) after I ended a 6 year relationship. Sure, it could have been a rebound, but we are doing better than me and 6-year-guy ever did, 2.5 years in. Sure, he had to put up with a little drama, more on the part of others than me, though. But, quite frankly, I spent the last year of my relationship preparing for it to end, so I wasn’t really in a bad state when it ended– plus, I broke up with him.
    Just because it was nine years doesn’t mean she’s still a mess about it. It doesn’t means she isn’t, either. You know her better than we do– if you feel like it could be something, you know the risks as well as we do!

  28. [F]oxymoron says:

    I agree with Ibluca77 above…

    … that being said, I see nothing wrong with a little nude sunbathing, as long as you both are honest and up front with each other

  29. brandy says:

    BFF, if we waited until things were perfect, nothing would ever happen. Hmm, that’s me pretending to be insightful when honestly, I have no words of wisdom. Thank Jesus everyone on the internet is smarter than me. Listen to them. (And yes, this will be the only time when I tell you to listen to other people rather than me)

    I ALMOST threw out an emoticon but I’m just not feeling it today. Let’s pray this feeling sticks.

  30. La Petite Belle says:

    I agree. Proceed.. but with caution. I guess you answered your own question with your post title, my friend!

  31. AuburnKat says:

    I can tell you one thing Matt, it doesn’t matter how much I’m into a guy, if he accidently says “my fiance” about his ex, it’s over for me. I also, I guess you could say am a bit hardened from my past relationships and don’t see any point in wasting my time.

    That being said, you have to do what your gut is telling you to do.

  32. CourtneyRyan says:

    I agree with most of what’s up there…keep your distance - friends are fine and remember that there are allllll sorts of friends!

    Are you fascinated with what you can’t really have, or genuinely interested in her?

  33. Mermanda says:

    Is she worth waiting around for? If you feel something special for her… maybe so. Give her a little space and time. If not… move on.

  34. Maxie says:

    If you like her enough, wait. You’ll be kicking yourself for years if you don’t. You’ll always wonder what if…

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