Where is the line between Assertiveness and Coming on Too Strong?

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DeathStarWithAFedora asks

I [M20’s] met a girl [F20’s] through a mutual friend and I really like her. I’m going to a small party she’s throwing soon and I want to show her I’m interested without coming on too strong. I’m new to this kind of thing and would appreciate some advice regarding a situation like this.


Demetrius says:

A¬†question for you before we start, how well do you know her? Is this someone who is a close friend of a mutual friend, or a girl you know through a friend who is attractive. That question is important because it changes your approach. If she’s someone you consider a friend, showing interest is a lot easier because you already know a little bit about each other. If she’s not close to you, you need to work to show you’re interested while also doing the work to see if she’s even interested in connecting with you at all. If she’s not a friend, you’ve got a little more work cut out for you but it’s not impossible.

If you’re already friends, you can start your escalation fairly earlier then the party. You can send her a text or FB message saying that you’ll be attending, that you’re looking forward to seeing her, and ask if you can help out in any way. She’ll probably decline the help, but it puts you into her mind as someone who is not only excited to see her, but also as someone who brings something to the table. Not figuratively speaking, and also possibly literally (she might actually ask you to bring something to the table like I dunno, dark rum). Once you’re at the party, bee-line to her, greet her very warmly, offer to help out, and then let her mingle. Don’t swarm her, but occasionally start-up conversations when you’re in her area. You don’t need to continually offer to help her out or anything, just be around, chat her up, and just try to be the guy who spoke to her that night, not the guy who was tagging behind her. At the end of the night, tell her you had a good time and mention that you guys should hang out sometime. You don’t need to say “this will be a date” but make sure you do it in a way that was flirty. You can go with something along the lines of “I had such a great time tonight, but the night would have been better if we got to talk more. We should¬†hang out sometime soon, when you’re not hosting a party”. It’s flirty enough where she’ll know you’re interested, but not so aggressive that it sounds like you’re asking her to sleep with you that night.

If you’re not already friends, you’ll be in a tougher, but not impossible position. Sending a pre-party message is a bad idea, but having your mutual friend relay that message is a good alternative. Have your friend say “My friend wants to know if he should bring anything in particular or if he can help out in any way”. Again, you want to be the person to offered to help and reached out. She’ll probably say no, but then you have a great opener when you see her. When you do see her, greet her, introduce yourself if you’ve never met, and thank her for hosting the party. Offer to help, which she’ll probably decline, then mingle for a bit. Come back later, like say 30 – 60 minutes later and chat her up briefly. Tell her how much you’re enjoying yourself, then start asking about her. Do you host parties often? How do you know our mutual friend? Then you move into more personal questions. You don’t need to ask her measurements or anything, just try to learn a little bit more about her. Is she from wherever you live or a transplant? What does she do in her spare time? If she’s a student, ask about what she’s studying. Things like that. The goal here is to build up a conversation that can be restarted at a later date. At the end of the night, thank her again, and then ask her if she’d like to hang out sometime. At this point, if she gives an answer that sounds positive, ask her for her number. If she seems hesitant, it probably means that she’s not interested.

Keep in mind that she could have a boyfriend/significant other or she could just not be interested. In that case, it wont matter if you weren’t aggressive enough or too aggressive, so don’t worry if you feel like you came on too strong and got rejected. I’m sure she’s very cool, but if she doesn’t seem to reciprocate your attraction, move on and don’t hold a grudge.

Good Luck Out There.

Demetrius Figueroa

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

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