How long do you hedge your bet?

You’ve been seeing someone casually, once a week for a month. You like him, he seems to like you as he keeps asking you to lunch, and ending each encounter with a passionate kiss. He calls you a few times a week and engages in an IM chat at least once a day.

You’re not smitten with him, but you like him. He’s intelligent, funny, attentive, self-aware, doesn’t press himself on you physically beyond the kiss, talks about waiting to get sexual until the time is right. Great, huh?

But meanwhile you continue to accept other invitations. Most are just one-time coffee meetings with nice guys but not any mutual spark.

Then — wham — a new guy comes on the scene that takes you aback. You have one date, then due to scheduling mismatches a week passes. He calls you several times a day and tells you how much he likes you. You like him, too, in a different way than the aforementioned guy.

But you’ve had this happen before. Part of you feels like you should tell the first guy that you’ve met someone new, but you also know that New Guy could go poof any time.

I described a similar circumstance in “The two-suitor conundrum: What would you do?” But that situation was different in that I hadn’t met one of the parties, although he called me every day for three months before deciding to fly to meet me. And as it turned out, the newer guy went poof soon after that was written. And the out-of-towner went poof, it just took another month.

How long can you have your feet in both camps? It’s not like you’re longing for one when you’re with the other. If you were, the decision would be easy. Neither of them knows there are others, as things haven’t heated up enough for that to seem relevant.

My rule of thumb is: when things look like they will heat up, that is the time to decide. Ideally beforehand, not afterward. Then you’ll be thinking with your brain, not other parts of your body. You tell one that you need to let him go, as you don’t want to be intimately involved with two at once — this would not be good for anyone.

Don’t hedge too long, or the second in line will feel used. You know how you’d feel if someone strung you along. As I mentioned in “Dating with integrity” it is sometimes hard to be 100% honest if you want to be sensitive to someone’s feelings. And while most who’ve dated online for long understand there will be others vying for your attention during the initial stages of getting to know each other, after seeing each other a while, it’s important to let someone go who you think isn’t a good match. The hard part is when you are dating two people you think are both a good match. The deciding is difficult.

What are your guidelines for when to let someone go if you’ve been seeing two people concurrently? How long will you see both before forcing yourself to make a decision?

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9 responses to “How long do you hedge your bet?”

  1. sd Avatar

    Most important question:
    Did you actually say that neither KNOW that you are still actively soliciting and dating others?

    I thought you were up-front about the open to other dating scenario with all of them that made it past coffee…

    That rule about pre-initimacy decisions only makes sense if ALL parties KNOW about the dating reality- otherwise, you are playing unfair with other people’s minds and hearts.

    Do you think that neither of them are dating or still soliciting dates from others?
    Would it suprise or disturb you if they were when they had given the impression they were focused entirely on building a potential relationship with you?

    Why do you think new guy deserves more concern than first guy?
    You are worried about HIM feeling used- but what about the guy that’s spent a month wooing and talking future?

    I would say the communications, dates, and kisses, and ESPECIALLY the respect and ‘future talk’ about stepping the relationship up of guy #1 means he thinks it’s just between you and him.

    Time to clarify in a hurry and risk him stepping back or away, or stop cold turkey (including new guy) and give this one a chance to bloom.

    New guy might be doing the sparks thing, but one meet in 2 weeks and the full court press wooing on the phone… have you seen it before?
    Did any of those pan out?
    Were they just going all out to see how far you were willing to take it in a short window?

    Are you willing to toss #1 for a shot that #2 sticks around?

  2. Christine Avatar

    I don’t think anyone feels “used” if they’ve been told upfront that other dating is happening. I think it’s when the other party chooses not to listen that there may be others that the trouble begins. I know I’ve experienced this both ways. When a man tells me upfront he is “dating”, sometimes when I really like him I tune that out and hope that in the end he “picks” me as an exclusive! Usually, I keep my options open until it’s really clear it’s going to be serious with someone. This generally means I’m not sleeping with anyone and just enjoying hanging out with different people.

  3. Christine Avatar

    P.S. Personally, I’d like more opportunity to “hedge my bet” or juggle more than one suitor, as they say. Some problems don’t seem so bad….

  4. nysharon Avatar

    YOU DON’T HAVE TO DECIDE AT THIS POINT. I think you should tell both that you are dating others and that you would like to get to know them better. You can date both at the same time and it will be clear eventually who you prefer over time (and who is worthy). It will also give “new guy sparks” time to make a more diligent play in pursuing you, if he is really interested. Promise to tell them as soon as you know how you feel. As said above, keep your options open, have fun. Don’t get intimate because it’s not fair and it puts you in the justifing zone.

  5. PreviouslyQueenofE Avatar

    Wait. One date, and he’s calling you several times a day telling you how much he likes you???? Wasn’t there a recent post about neediness? You may feel more of a spark with new guy than with mr. wait for the good stuff, but seriously…give it a couple of more dates before making any moves. Like nysharon says, you don’t have to decide, and why would you, with such limited data?

    Obviously this is much easier to tell someone else to do, than do it one-self.

  6. bookyone Avatar

    Hi DG,

    So, you’re multidating now? All right, you go, girlfriend! (Not bad street for a 40-ish white women, huh)? ๐Ÿ™‚

    Personally, I don’t see anything wrong with gals multidating. Guys do it all the time, and it seems to work pretty well, because you rarely hear of a guy lamenting a lost girlfriend, (country western songs and songwriters excepted), they just move on to the next one in line. IMHO, if we ladies did this, not only would it help to boost our collective egos, but it might just give the guys the kick in the pants they need to make it official, if they knew they had competition for our hearts. ๐Ÿ™‚

    Best wishes and happy dating to you from bookyone ๐Ÿ™‚

  7. hunter Avatar

    to bookyone,

    there is light at the end of the tunnel, I heard a female therapist say, that, after a certain age, women intellectualize, allowing them to possibly mutlidate, if they want to….

  8. hunter Avatar


    Which one accepts your contract? The one about, weekly social and sexual exclusivity and continuity. Or whatever your contract is, see each other every two weeks, one phone call a week, etc….

  9. greendaze44 Avatar

    I agree with the concept of not having anough data yet. And I would look closely at what attracts you more to the new one. Is the first one not exciting enough, so he seems boring even though he is more steady? Is the second one more exciting just because he adds competion to the whole situation? Or maybe because he is from out of town and has put a lot of effort in seeing you?
    I don’t think that just because we get involved quickly in a relationship that it always has to do with neediness. I think most women like the idea that some guy just goes crazy over us. We think, “Hey, after all these losers who didn’t appreciate me, someone finally does!” And I think we still want that easy storybook love story, it was love at first site, we clicked immediatley and we’ve been together every since. Wouldn’t that be great and easy?
    I think you should continue dating both and get more info first. I also don’t feel they need to know about the other. You are an adult and have the right to see who you want to see, when you want to see them.
    Have fun and enjoy life…………………