I’m not into her. Am I leading her on?

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Advise54321 asks:

Just a bit of background. I’ve been on a couple of dates with a woman but unlike dates I’ve had before, I never felt nervous or excited. She’s nice, beautiful and funny but, I don’t feel anything.

This is the first woman I have dated that I didn’t have a chance to get to know before dating i.e. haven’t had the chance to speak to her before “hit on her” and asked her out. So it might be that I don’t know her as well enough as others I have dated or have had a chance to develop feelings but, I don’t know. I feel a little off dating her because she seems a lot more interested in dating than I do.

So two questions:

How long until you should “feel” if you’re interested in dating someone?
How long until I am leading her on by dating her with out an “emotional connection/investment”?


Demetrius says:

This holiday season, if you’re wondering what to get me, please give me the present of “I asked a succinct question instead of a gobbledygook statement that requires interpretation” because I well and truly will appreciate it. It would really be in the spirit of Ujima, you know? Anyway I appreciate the succinct questions, and I hope I can give a succinct answer.

This is a tough situation, but a fairly common one. I always say that it’s tougher to date someone who is nice who you aren’t into versus someone who is absolutely terrible. It’s so much easier to reject an asshole than a nice person who just doesn’t click. It gets especially hard if you are generally nice and a good catch on paper, because they wont immediately want to drop you either. I say this as someone who has been in this situation a bunch of times, or at least, I used to happen to me a lot It stopped happening as I got older because I got really good at learning the difference between “I should be attracted to you” and “I should be attracted to you because it makes sense, but the heart wants what the heart wants”. It’s a special kind of skill, so it’s okay if you don’t have it yet.

Here’s a bit of Storytime with Demetrius. Once upon a time I went on 3 dates with a very lovely, very sweet girl. Our first date was at the best Chinese (American) spot in Manhattan (Shoutout to Wo Hop. If you go, make sure to eat in the basement, not the upper level restaurant. It’s worth the wait), then followed that up with drinks at a very cool dive bar (Shoutout to Fontana’s), we walked to the train in the snow and I thought, “Wow, this was an adequate date with a nice person”. No sparks, no first kiss. The 2nd date involved drinks and dinner at a very cool restaurant which is now closed (RIP The Beast, you will be missed), we walk to the train, hug goodbye and part ways. No sparks, no first kiss. The 3rd date is over New Year’s Eve. I meet her friends at a house party in Greenpoint and everyone seems to enjoy my presence there, except her. She’s distant, seems disinterested in engaging with me, and makes it a point to be not within 6 feet of me when the ball drops. I leave at 12:30am, realizing that while I should have been attracted to her, and she probably felt the same, the spark just wasn’t there.

After these dates, I come up with a pretty clear criteria for whether or not I should date someone, that I think might be a good idea for you to try to implement. If you haven’t kissed by the third date, that’s a bad sign. If you don’t feel a spark or excitement by the third date, that’s a bad sign. If you get both of those signs, drop them (as politely as possible of course). It’s entirely possible that you should be into someone, but just aren’t. The modern dating atmosphere tends to focus in on the dichotomy between “OMG AMAZE FIRST DATE YOU GUISE” or “WORST DATE EVER, DEETS ON MY TWITTER/BLOG!” which is fine, no shade, it’s just not my cup of tea. For the most part I find that most daters have a more nuanced experience. I’ve been on more mediocre dates then I have truly bad dates. Whether that’s because I’m a straight man, or the fact that I plan the dates, or the fact that I screen fairly well, who knows. I do know that most people have more  “blah” dating experiences more often than “This guy said he didn’t bring his wallet and I had to pay for everything!”.

Anyway, back to your actual questions. How long should you wait to feel if you’re interested in dating someone? I’d say 3 dates is a great timeframe for whether or not you really are interested in someone. Unless you’re dealing with a recent breakup, or a similar situation where you’ve got lingering feelings for someone else, going on 3 dates with someone will usually tell you all you need to know about whether or not there is something there. If you move a little slower than that, I’d say 5 dates, but beyond that, you might as well switch over to a platonic relationship. Whether or not you’re leading someone on while continuing to see them is a bit more tricky. I think that unless you specifically lie, you aren’t really leading someone on a lot of the time. If she asks what you feel about her and you’re honest, how could you be leading her on. If she doesn’t ask, and you’re up to date #4, I don’t think you’re leading her on. If you want to be on the safe side, you can always sit her down and tell her where you stand.

If you’re worried about leading her own, start communicating. If she really is more interested in dating than you are, then telling her where you stand might prompt her to end things. Which, based on your situation, you should probably do. I’m not saying that after a couple dates you need to be in love, but at minimum you should know if you want to go on another date. Not in the “Eh, I guess I’ll do another date” and more of the “I totally want to go on another date and see where things go!” sort of way. The fact that you have these doubts says a lot, so listen to what your subconscious is trying to tell you.

If you’re worried about leading her on, be honest, and deal with the fallout.

Good Luck Out There.

Demetrius Figueroa

Demetrius is a sex, dating, and relationship writer based in Brooklyn.

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