(Closed) Entice an Older Man to Approach You?

posted 4 years ago in Relationships
Post # 2
720 posts
Busy bee
  • Wedding: February 2015

Where did you meet him? Work? School? 

Post # 3
3468 posts
Sugar bee
  • Wedding: July 2015

Have you talked to him before? If you’re over 21…hoping you are….invite him out for a drink or something casual since you aren’t looking for anything serious.

Post # 4
1729 posts
Bumble bee
  • Wedding: June 2014

Well, I don’t have much experience reeling in guys but I think that if he’s already admiring you from afar, you’re halfway there. If you know he’s single, I say go for it. When you catch him looking at you, hold his gaze for a few seconds longer than normal. Do you have an opportunity to talk to him regularly? 

Post # 6
4245 posts
Honey bee

Why do you need to entice him to approach you? Why don’t you just approach him and ask him to dinner or to go out for a drink (or the movies, or a walk, or to a concert…) 🙂

Post # 8
260 posts
Helper bee
  • Wedding: May 2014


cooperhook:  like you I’m not really the type to approach someone and would rather them approach me. My husband is 10 years older than me. He was working when I met him and  when I first laid my eyes on him, he was my dream guy. Corny, I know. Lol. My perfect ideal of a type of guy I wanted physically and I got lucky that his personality was even better. 

Well, like you, he was working and I didn’t want to bother him and come off as this young girl who is bothering him. Although I was 27 and he was 36, I look younger than my age and he accident thought I was 23 at the time. He actually told me he was second guessing about talking to me because he thought I was too young. Lol. But When he gave me eye contact and smiled, that was my cue and I did  approach him thinking he was going to reject me, lol and asked if he had a gf. He said no and I asked for his number. He gave it to me and that night I txtd him, ” it was nice meeting you” that way he had my number now and the ball was in his court to contact me for a date. Lol. 

So in other words, I say the next time he makes contact with you, just ask him if he’s single and ask if he’ll like to go out for a drink some time or maybe just give him your number. Of course only if he says he’s single. Lol Good luck! Let us know how it goes. 

Post # 10
1212 posts
Bumble bee

Next time you see him looking at you just catch his eye smile SWEETLY and raise a hand in a short wave as in a gently finger wiggle wave or an air salute wave, keep it short, then go back to whatever you’re doing. A couple moments later glance back up. If he’s looking at you again give him a SULTRY half smile this time, hold his gaze for a moment, then turn away and get on with your life.

Youve just given him sweet and approachable with a hint of mystery sexy in under 30 seconds. If that doesn’t move things forward with him approaching you then you need to just walk up and say hi. “Hi there, I see you over here all the time and thought I should probably say hi, I’m Cooperhook.”


Post # 11
3297 posts
Sugar bee
  • Wedding: October 2010

How about walking up to him and saying hi? That way, you are only being friendly without coming on too strong. 

Post # 12
304 posts
Helper bee
  • Wedding: July 2014

I have ALWAYS dated older men….the thing is, if he’s older and the “head honcho” he’s probably got a pretty good head on his shoulders so you need dig up whatever confidence you can find, and approach him.  If you act all shy and standoffish, it gives him too much of an opportunity to “talk himself out of” approaching you…if you want it, go after it.  And for the record, older men are where it’s at….especially if he’s divorced.  Divorced men are one of the best kept secrets.  Meow!

Post # 13
2167 posts
Buzzing bee
  • Wedding: May 2014

cooperhook:  Well if you just want to bone him (and it sounds like you do), just invite him out for a drink and if he’s into you the rest should take care of itself. Not hard to get a man to hop into bed with you if that’s all you’re looking for. 

Post # 14
5857 posts
Bee Keeper

cooperhook:  My husband’s 8 years older than me.  Apparently what caught his eye was I was pretty, what made him stay was my personality (isnt’ that what they all say?) but it was the truth.  It took a month of talking (him hitting on me repeatedly) before we went out with co-workers to a bar to get some drinks. Needless to say we slept together that night (and the rest is history).

So my advice?  Keep it casual – invite him to a drink to a bar and find some place in the conversation to say you want to jump him.  No on a serious note, just be cool and be friendly.  He may not be the type of guy to sleep around with just anyone.  My husband wasn’t.  The last person he slept with?  He married.  So make sure you’re not giving off “Hey I’ll sleep with anything that walks” vibe because that can be a turn off as well.  be yourself and ask him to do something together.

Post # 15
355 posts
Helper bee
  • Wedding: May 2015 - The Fairmont, SF

mrs.joiner:  That’s so true! My Fiance is 16 years older than I am (22 & almost 38) and he always says what really drew him to me is that I’m clever and funny. At his age, he said that there were dozens of pretty girls he could’ve easily had but he had zero interest because they bored him. 

He also said that long before we got together, he told himself that the next girl he slept with, he was going to marry (as in, he wasn’t looking to hook up or have a fling with someone he couldn’t see himself getting serious with) and, hey, that obviously held true. 

cooperhook:  I’d personally try to chat with the guy a bit more before pouncing and assess whether or not he’s truly interested or just friendly. Going straight in for the kill may come off as desperate, especially if he’s the head honcho and attractive, as I’d imagine he gets a lot of female attention. If he does seem genuinely keen, keep it casual and ask him out for a drink. Also, don’t be offended if he turns you down – it might be an age thing or he could be in a relationship.

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